organic compounds
Ethyl 2-(4-methylbenzoyl)-2,3-dihydro-1H-indene-2-carboxylate
aKey Laboratory of Pesticides and Chemical Biology of the Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
*Correspondence e-mail: qwjgq@163.com
The title compound, C20H20O3, contains two fused rings with a quaternary carbon centre connecting p-toluoyl and ethoxycarbonyl groups. The dihedral angle between the fused benzene ring and the three-C-atom plane (derived from O=C—C—C=O) is 82.5 (4)°, whereas the dihedral angle between the planes of the benzene rings is 53.4 (2)°. In the crystal, molecules are linked via C—H⋯Oester hydrogen bonds, forming chains propagating along [010].
Related literature
For the preparation and crystal engineering studies of the title compound, see: Singh & Paul (2006); Wang & Wu (2012).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2004); cell SAINT(Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536813005801/gg2108sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536813005801/gg2108Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536813005801/gg2108Isup3.cml
The title compound was synthesized according to the reported method (Singh et al.; 2006 and Wang et al.; 2012). The ethyl 3-oxo-3-(p-tolyl)propanoate reacts with 1,2-bis(halomethyl)benzene to obtain the title compound via a two-step C-alkylation process. Crystals of (I) suitable for X-ray diffraction were grown by slow evaporation of a acetic ether solution of the title compound (I) at 293 K.
Data collection: APEX2 (Bruker, 2004); cell
SAINT(Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. A view of (I), showing the atom-labelling scheme, with displacement ellipsoids drawn at the 30% probalility level. |
C20H20O3 | F(000) = 656 |
Mr = 308.37 | Dx = 1.238 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3624 reflections |
a = 8.1957 (14) Å | θ = 2.5–24.5° |
b = 6.1287 (10) Å | µ = 0.08 mm−1 |
c = 32.995 (5) Å | T = 298 K |
β = 93.014 (3)° | Block, colourless |
V = 1655.0 (5) Å3 | 0.12 × 0.10 × 0.10 mm |
Z = 4 |
Bruker APEXII CCD diffractometer | 3241 independent reflections |
Radiation source: fine-focus sealed tube | 2482 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ϕ and ω scans | θmax = 26.0°, θmin = 1.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −10→10 |
Tmin = 0.990, Tmax = 0.992 | k = −7→7 |
11945 measured reflections | l = −40→36 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.187 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.1176P)2 + 0.1336P] where P = (Fo2 + 2Fc2)/3 |
3241 reflections | (Δ/σ)max = 0.008 |
210 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
C20H20O3 | V = 1655.0 (5) Å3 |
Mr = 308.37 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.1957 (14) Å | µ = 0.08 mm−1 |
b = 6.1287 (10) Å | T = 298 K |
c = 32.995 (5) Å | 0.12 × 0.10 × 0.10 mm |
β = 93.014 (3)° |
Bruker APEXII CCD diffractometer | 3241 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | 2482 reflections with I > 2σ(I) |
Tmin = 0.990, Tmax = 0.992 | Rint = 0.025 |
11945 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
wR(F2) = 0.187 | H-atom parameters constrained |
S = 1.09 | Δρmax = 0.27 e Å−3 |
3241 reflections | Δρmin = −0.25 e Å−3 |
210 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.7866 (3) | 0.2221 (4) | 0.25704 (6) | 0.0666 (6) | |
H1 | 0.8421 | 0.2668 | 0.2809 | 0.080* | |
C2 | 0.8114 (3) | 0.0156 (4) | 0.24231 (7) | 0.0693 (6) | |
H2 | 0.8860 | −0.0765 | 0.2559 | 0.083* | |
C3 | 0.7266 (2) | −0.0567 (3) | 0.20748 (6) | 0.0555 (5) | |
H3 | 0.7424 | −0.1972 | 0.1978 | 0.067* | |
C4 | 0.6182 (2) | 0.0832 (3) | 0.18736 (5) | 0.0463 (4) | |
C5 | 0.5970 (2) | 0.2939 (3) | 0.20139 (5) | 0.0452 (4) | |
C6 | 0.6805 (2) | 0.3627 (3) | 0.23682 (6) | 0.0552 (5) | |
H6 | 0.6647 | 0.5027 | 0.2467 | 0.066* | |
C7 | 0.4828 (3) | 0.4205 (3) | 0.17361 (7) | 0.0626 (6) | |
H7A | 0.5406 | 0.5355 | 0.1602 | 0.075* | |
H7B | 0.3963 | 0.4854 | 0.1885 | 0.075* | |
C8 | 0.5092 (3) | 0.0359 (3) | 0.15049 (7) | 0.0655 (6) | |
H8A | 0.4358 | −0.0840 | 0.1556 | 0.079* | |
H8B | 0.5732 | −0.0015 | 0.1276 | 0.079* | |
C9 | 0.4114 (2) | 0.2508 (3) | 0.14203 (6) | 0.0514 (5) | |
C10 | 0.2314 (3) | 0.2265 (3) | 0.14927 (6) | 0.0555 (5) | |
C11 | −0.0233 (3) | 0.4180 (4) | 0.14107 (7) | 0.0726 (7) | |
H11A | −0.0434 | 0.4237 | 0.1698 | 0.087* | |
H11B | −0.0798 | 0.2922 | 0.1293 | 0.087* | |
C12 | −0.0820 (3) | 0.6211 (5) | 0.12057 (9) | 0.0863 (8) | |
H12A | −0.0303 | 0.7449 | 0.1336 | 0.129* | |
H12B | −0.1983 | 0.6324 | 0.1222 | 0.129* | |
H12C | −0.0554 | 0.6173 | 0.0926 | 0.129* | |
C13 | 0.4316 (2) | 0.3270 (3) | 0.09827 (6) | 0.0516 (5) | |
C14 | 0.3593 (2) | 0.1945 (3) | 0.06402 (6) | 0.0513 (5) | |
C15 | 0.3657 (3) | 0.2784 (4) | 0.02492 (7) | 0.0676 (6) | |
H15 | 0.4123 | 0.4147 | 0.0212 | 0.081* | |
C16 | 0.3042 (3) | 0.1633 (5) | −0.00819 (7) | 0.0791 (7) | |
H16 | 0.3093 | 0.2236 | −0.0340 | 0.095* | |
C17 | 0.2350 (3) | −0.0398 (5) | −0.00395 (7) | 0.0705 (7) | |
C18 | 0.2282 (3) | −0.1239 (4) | 0.03492 (7) | 0.0665 (6) | |
H18 | 0.1819 | −0.2607 | 0.0385 | 0.080* | |
C19 | 0.2881 (2) | −0.0102 (3) | 0.06837 (6) | 0.0578 (5) | |
H19 | 0.2811 | −0.0703 | 0.0941 | 0.069* | |
C20 | 0.1698 (4) | −0.1689 (6) | −0.04011 (8) | 0.1051 (11) | |
H20A | 0.2398 | −0.2916 | −0.0442 | 0.158* | |
H20B | 0.1664 | −0.0777 | −0.0638 | 0.158* | |
H20C | 0.0616 | −0.2196 | −0.0354 | 0.158* | |
O1 | 0.1677 (3) | 0.0787 (3) | 0.16597 (5) | 0.0896 (6) | |
O2 | 0.15098 (16) | 0.4028 (2) | 0.13532 (4) | 0.0625 (4) | |
O3 | 0.5094 (2) | 0.4910 (3) | 0.09153 (5) | 0.0775 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0753 (13) | 0.0748 (15) | 0.0488 (11) | −0.0053 (11) | −0.0071 (9) | −0.0038 (10) |
C2 | 0.0733 (13) | 0.0787 (15) | 0.0548 (12) | 0.0152 (12) | −0.0078 (10) | 0.0051 (11) |
C3 | 0.0662 (12) | 0.0488 (11) | 0.0516 (11) | 0.0107 (9) | 0.0038 (9) | 0.0000 (8) |
C4 | 0.0530 (9) | 0.0411 (9) | 0.0452 (9) | 0.0012 (7) | 0.0056 (7) | −0.0007 (7) |
C5 | 0.0496 (9) | 0.0402 (9) | 0.0465 (10) | −0.0029 (7) | 0.0097 (7) | −0.0031 (7) |
C6 | 0.0675 (11) | 0.0487 (11) | 0.0502 (11) | −0.0103 (9) | 0.0109 (9) | −0.0092 (8) |
C7 | 0.0749 (13) | 0.0380 (10) | 0.0738 (14) | 0.0074 (9) | −0.0077 (10) | −0.0111 (9) |
C8 | 0.0928 (15) | 0.0363 (10) | 0.0649 (13) | 0.0133 (9) | −0.0206 (11) | −0.0072 (9) |
C9 | 0.0586 (10) | 0.0358 (9) | 0.0589 (11) | 0.0047 (8) | −0.0059 (8) | −0.0017 (8) |
C10 | 0.0712 (12) | 0.0477 (11) | 0.0480 (10) | −0.0093 (9) | 0.0066 (9) | 0.0021 (8) |
C11 | 0.0517 (11) | 0.1032 (19) | 0.0637 (13) | −0.0118 (11) | 0.0122 (9) | −0.0123 (13) |
C12 | 0.0489 (12) | 0.108 (2) | 0.1017 (19) | 0.0111 (12) | 0.0005 (11) | −0.0099 (16) |
C13 | 0.0441 (9) | 0.0453 (10) | 0.0659 (12) | 0.0038 (8) | 0.0074 (8) | 0.0053 (9) |
C14 | 0.0455 (9) | 0.0539 (11) | 0.0550 (11) | 0.0080 (8) | 0.0078 (7) | 0.0051 (8) |
C15 | 0.0675 (12) | 0.0726 (14) | 0.0641 (13) | 0.0099 (11) | 0.0151 (10) | 0.0132 (11) |
C16 | 0.0814 (15) | 0.104 (2) | 0.0525 (13) | 0.0238 (15) | 0.0096 (11) | 0.0089 (13) |
C17 | 0.0571 (11) | 0.0984 (18) | 0.0555 (13) | 0.0277 (12) | −0.0020 (9) | −0.0150 (12) |
C18 | 0.0634 (12) | 0.0707 (14) | 0.0649 (13) | 0.0048 (10) | −0.0021 (9) | −0.0147 (11) |
C19 | 0.0625 (11) | 0.0587 (12) | 0.0521 (11) | 0.0014 (9) | 0.0013 (8) | 0.0008 (9) |
C20 | 0.097 (2) | 0.146 (3) | 0.0700 (16) | 0.0411 (19) | −0.0142 (14) | −0.0384 (17) |
O1 | 0.1113 (14) | 0.0733 (11) | 0.0858 (13) | −0.0225 (10) | 0.0211 (10) | 0.0235 (9) |
O2 | 0.0509 (8) | 0.0652 (9) | 0.0725 (9) | 0.0009 (6) | 0.0132 (6) | 0.0094 (7) |
O3 | 0.0783 (10) | 0.0644 (9) | 0.0909 (12) | −0.0230 (8) | 0.0139 (9) | 0.0072 (8) |
C1—C6 | 1.372 (3) | C11—C12 | 1.484 (4) |
C1—C2 | 1.374 (3) | C11—H11A | 0.9700 |
C1—H1 | 0.9300 | C11—H11B | 0.9700 |
C2—C3 | 1.384 (3) | C12—H12A | 0.9600 |
C2—H2 | 0.9300 | C12—H12B | 0.9600 |
C3—C4 | 1.379 (3) | C12—H12C | 0.9600 |
C3—H3 | 0.9300 | C13—O3 | 1.216 (2) |
C4—C5 | 1.385 (2) | C13—C14 | 1.489 (3) |
C4—C8 | 1.499 (3) | C14—C15 | 1.392 (3) |
C5—C6 | 1.389 (3) | C14—C19 | 1.395 (3) |
C5—C7 | 1.493 (3) | C15—C16 | 1.374 (4) |
C6—H6 | 0.9300 | C15—H15 | 0.9300 |
C7—C9 | 1.564 (3) | C16—C17 | 1.378 (4) |
C7—H7A | 0.9700 | C16—H16 | 0.9300 |
C7—H7B | 0.9700 | C17—C18 | 1.386 (3) |
C8—C9 | 1.559 (3) | C17—C20 | 1.506 (3) |
C8—H8A | 0.9700 | C18—C19 | 1.374 (3) |
C8—H8B | 0.9700 | C18—H18 | 0.9300 |
C9—C10 | 1.514 (3) | C19—H19 | 0.9300 |
C9—C13 | 1.535 (3) | C20—H20A | 0.9600 |
C10—O1 | 1.195 (2) | C20—H20B | 0.9600 |
C10—O2 | 1.335 (3) | C20—H20C | 0.9600 |
C11—O2 | 1.454 (2) | ||
C6—C1—C2 | 120.55 (19) | O2—C11—H11A | 110.3 |
C6—C1—H1 | 119.7 | C12—C11—H11A | 110.3 |
C2—C1—H1 | 119.7 | O2—C11—H11B | 110.3 |
C1—C2—C3 | 120.7 (2) | C12—C11—H11B | 110.3 |
C1—C2—H2 | 119.6 | H11A—C11—H11B | 108.6 |
C3—C2—H2 | 119.6 | C11—C12—H12A | 109.5 |
C4—C3—C2 | 118.89 (19) | C11—C12—H12B | 109.5 |
C4—C3—H3 | 120.6 | H12A—C12—H12B | 109.5 |
C2—C3—H3 | 120.6 | C11—C12—H12C | 109.5 |
C3—C4—C5 | 120.47 (17) | H12A—C12—H12C | 109.5 |
C3—C4—C8 | 127.69 (17) | H12B—C12—H12C | 109.5 |
C5—C4—C8 | 111.81 (16) | O3—C13—C14 | 120.20 (19) |
C4—C5—C6 | 119.98 (18) | O3—C13—C9 | 120.44 (18) |
C4—C5—C7 | 111.40 (16) | C14—C13—C9 | 119.33 (16) |
C6—C5—C7 | 128.61 (17) | C15—C14—C19 | 117.6 (2) |
C1—C6—C5 | 119.33 (19) | C15—C14—C13 | 117.97 (19) |
C1—C6—H6 | 120.3 | C19—C14—C13 | 124.38 (17) |
C5—C6—H6 | 120.3 | C16—C15—C14 | 121.1 (2) |
C5—C7—C9 | 105.30 (15) | C16—C15—H15 | 119.4 |
C5—C7—H7A | 110.7 | C14—C15—H15 | 119.4 |
C9—C7—H7A | 110.7 | C15—C16—C17 | 121.3 (2) |
C5—C7—H7B | 110.7 | C15—C16—H16 | 119.4 |
C9—C7—H7B | 110.7 | C17—C16—H16 | 119.4 |
H7A—C7—H7B | 108.8 | C16—C17—C18 | 117.8 (2) |
C4—C8—C9 | 105.09 (15) | C16—C17—C20 | 121.6 (3) |
C4—C8—H8A | 110.7 | C18—C17—C20 | 120.5 (3) |
C9—C8—H8A | 110.7 | C19—C18—C17 | 121.6 (2) |
C4—C8—H8B | 110.7 | C19—C18—H18 | 119.2 |
C9—C8—H8B | 110.7 | C17—C18—H18 | 119.2 |
H8A—C8—H8B | 108.8 | C18—C19—C14 | 120.5 (2) |
C10—C9—C13 | 109.40 (15) | C18—C19—H19 | 119.8 |
C10—C9—C8 | 112.61 (16) | C14—C19—H19 | 119.8 |
C13—C9—C8 | 110.23 (16) | C17—C20—H20A | 109.5 |
C10—C9—C7 | 107.08 (16) | C17—C20—H20B | 109.5 |
C13—C9—C7 | 111.68 (16) | H20A—C20—H20B | 109.5 |
C8—C9—C7 | 105.78 (15) | C17—C20—H20C | 109.5 |
O1—C10—O2 | 123.5 (2) | H20A—C20—H20C | 109.5 |
O1—C10—C9 | 126.9 (2) | H20B—C20—H20C | 109.5 |
O2—C10—C9 | 109.51 (15) | C10—O2—C11 | 118.56 (16) |
O2—C11—C12 | 106.95 (18) | ||
C6—C1—C2—C3 | −1.9 (3) | C8—C9—C10—O2 | −169.98 (16) |
C1—C2—C3—C4 | 1.0 (3) | C7—C9—C10—O2 | 74.16 (19) |
C2—C3—C4—C5 | 1.2 (3) | C10—C9—C13—O3 | 124.95 (19) |
C2—C3—C4—C8 | −177.0 (2) | C8—C9—C13—O3 | −110.7 (2) |
C3—C4—C5—C6 | −2.5 (3) | C7—C9—C13—O3 | 6.6 (2) |
C8—C4—C5—C6 | 176.01 (18) | C10—C9—C13—C14 | −56.9 (2) |
C3—C4—C5—C7 | 176.28 (18) | C8—C9—C13—C14 | 67.4 (2) |
C8—C4—C5—C7 | −5.2 (2) | C7—C9—C13—C14 | −175.30 (15) |
C2—C1—C6—C5 | 0.6 (3) | O3—C13—C14—C15 | −8.0 (3) |
C4—C5—C6—C1 | 1.6 (3) | C9—C13—C14—C15 | 173.84 (16) |
C7—C5—C6—C1 | −176.9 (2) | O3—C13—C14—C19 | 170.76 (19) |
C4—C5—C7—C9 | 7.9 (2) | C9—C13—C14—C19 | −7.4 (3) |
C6—C5—C7—C9 | −173.47 (17) | C19—C14—C15—C16 | −0.1 (3) |
C3—C4—C8—C9 | 178.54 (18) | C13—C14—C15—C16 | 178.77 (18) |
C5—C4—C8—C9 | 0.2 (2) | C14—C15—C16—C17 | −0.4 (3) |
C4—C8—C9—C10 | −112.09 (18) | C15—C16—C17—C18 | 0.5 (3) |
C4—C8—C9—C13 | 125.43 (18) | C15—C16—C17—C20 | −179.0 (2) |
C4—C8—C9—C7 | 4.5 (2) | C16—C17—C18—C19 | 0.0 (3) |
C5—C7—C9—C10 | 112.94 (18) | C20—C17—C18—C19 | 179.4 (2) |
C5—C7—C9—C13 | −127.31 (17) | C17—C18—C19—C14 | −0.5 (3) |
C5—C7—C9—C8 | −7.4 (2) | C15—C14—C19—C18 | 0.6 (3) |
C13—C9—C10—O1 | 135.3 (2) | C13—C14—C19—C18 | −178.23 (18) |
C8—C9—C10—O1 | 12.4 (3) | O1—C10—O2—C11 | 0.7 (3) |
C7—C9—C10—O1 | −103.5 (2) | C9—C10—O2—C11 | −176.98 (16) |
C13—C9—C10—O2 | −47.0 (2) | C12—C11—O2—C10 | −176.51 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7A···O3 | 0.97 | 2.28 | 2.762 (3) | 110 |
C8—H8A···O1 | 0.97 | 2.45 | 2.883 (3) | 107 |
C1—H1···O1i | 0.93 | 2.60 | 3.357 (3) | 139 |
Symmetry code: (i) −x+1, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C20H20O3 |
Mr | 308.37 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 8.1957 (14), 6.1287 (10), 32.995 (5) |
β (°) | 93.014 (3) |
V (Å3) | 1655.0 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.12 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1997) |
Tmin, Tmax | 0.990, 0.992 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11945, 3241, 2482 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.187, 1.09 |
No. of reflections | 3241 |
No. of parameters | 210 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.25 |
Computer programs: APEX2 (Bruker, 2004), SAINT(Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O1i | 0.93 | 2.60 | 3.357 (3) | 139 |
Symmetry code: (i) −x+1, y+1/2, −z+1/2. |
Acknowledgements
The authors are grateful to the Central China Normal University for financial support and thank Dr Xiang-Gao Meng for the X-ray data collection.
References
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The title molecule (I)(Fig.1) was synthesized in a mixture of 1,4-dibromo-2,3- bis(bromomethyl)benzene (1.0 mmol), ethyl 3-oxo-3-(p-tolyl)propanoate (1.0 mmol) and Cs2CO3 (2 mmol) in DMSO (5 ml). The mixture was stirred at 40° for 30 min until almost full conversion of the substrates by TLC analysis. The resulting mixture was dropped into 100 ml 1 M HCl (aq) and extracted with EtOAc 3 times (3 times 50 ml). The organic extract was dried with Na2SO4, filtered and concentrated. The crude product was purified by column chromatography on silica gel (eluent: petroleum ether/EtOAc=50/1) to afford the product as a white solid.