(4-Ethylcyclohexyl)(4-methoxyphenyl)methanone

In the title compound, C16H22O2, the cyclohexane ring adopts a chair conformation and its mean plane subtends a dihedral angle of 54.2 (6)° with the benzene ring. The crystal structure is stabilized by van der Waals interactions only with no classical intermolecular hydrogen bonding observed.

In the title compound, C 16 H 22 O 2 , the cyclohexane ring adopts a chair conformation and its mean plane subtends a dihedral angle of 54.2 (6) with the benzene ring. The crystal structure is stabilized by van der Waals interactions only with no classical intermolecular hydrogen bonding observed.  supplementary materials . E69, o348 [doi:10.1107/S1600536813003279] (4-Ethylcyclohexyl)(4-methoxyphenyl)methanone Chun-Lei Ding, Yong-Jie Wu, Yi Zhang and Li Zhou Comment SGLT2 inhibitors are a new class of hypoglycemic agents, and the most advanced drug dapagliflozin has been approved recently in EU for the treatment of type 2 diabetes (Washburn, 2009). During the study on the SGLT2 inhibitors in our laboratory, the title compound was prepared which is a key intermediate for the synthetic procedure (Zhao et al., 2011;Shao et al., 2011).

Related literature
In the title compound, C 16 H 22 O 2 , bond lengths are normal and and in good agreement with those reported previously (Wang et al., 2011). The cyclohexane ring adopts a chair conformation and its least squares plane (C10/C11/C13/C14) is at an angle of 54.2 (6)° to the benzene ring (C2-C7). The crystal structure is stabilized by van der Waals interactions only with no classical inter-molecular hydrogen bonding observed.

Experimental
15.62 g (0.1 mol) of trans-4-ethylcyclohexanecarboxylic acid was stirred in 150 ml of dried CH 2 Cl 2 at room temperature.
17.80 g (0.13 mol) of freshly distilled oxalyl chloride was added dropwise followed by addition of 0.1 ml of dried DMF.
The mixture was stirred at room temperature for 5 h and evaporated in vacuo to give a residue. The residue was dissolved in 80 ml of dried dichloromethane followed by addition of 10.81 g (0.1 mol) of anisole. The mixture thus obtained was stirred at 0 o C followed by portionwise addition of 14.67 g (0.11 mol) of AlCl 3 . The reaction mixture was then stirred at room temperature overnight, poured into 300 ml of ice-water and extracted with 100 ml three times of dichloromethane.
The combined extracts were washed with brine, dried over Na 2 SO 4 and evaporated to dryness. The residue was purified by column chromatography to afford the pure title compound as colorless crystals. The single crystals suitable for singlecrystal X-ray diffraction were obtained by slow evaporation at room temperature of a 0.2 M solution of the title compound in dichloromethane/hexane (1/12 by v/v).

Refinement
All H atoms bonded on carbon were found on difference maps, with C-H = 0.95-1.00, and included in the final cycles of refinement using a riding model, with U iso (H) = 1.2U eq (C) and 1.5U eq (C) for the methyl H atoms.   Special details 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 F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.