Ethyl 2-[4-(benzyloxy)anilino]-4-oxo-4,5-dihydrofuran-3-carboxylate

In the title compound, C20H19NO5, the dihydrofuran ring is almost planar [maximum deviation of 0.021 (2)°] and makes dihedral angles of 28.1 (7) and 54.5 (5)° with the benzyl and phenylamino rings, respectively. The molecular packing is stabilized by intramolecular N—H⋯O hydrogen bonds and intermolecular C—H⋯O interactions.

In the title compound, C 20 H 19 NO 5 , the dihydrofuran ring is almost planar [maximum deviation of 0.021 (2) ] and makes dihedral angles of 28.1 (7) and 54.5 (5) with the benzyl and phenylamino rings, respectively. The molecular packing is stabilized by intramolecular N-HÁ Á ÁO hydrogen bonds and intermolecular C-HÁ Á ÁO interactions.
An ORTEP (Farrugia,1997) plot of the molecule is shown in Fig. 1. The bond lengths in (I) show normal values (Allen et al., 1987) and are comparable to the related structure (Erdsack et al., 2007). The dihydrofuran ring (O2/C1-C4) is planar with a maximum deviation of -0.021 (2)° for C3 from the least square plane defined by all non hydrogen atoms in the molecule. The dihydrofuran ring makes dihedral angles of 28.1 (7)° and 54.5 (5)°, respectively, with the benzyl ring (C12-C17) and phenylamino ring (C5-C10), whereas the benzyl and phenylamino rings are oriented at an angle of 78.6 (6)° with respect to each other.
The crystal structure is stabilized by intramolecular N-H···O interactions. In addition to the van der Waals interactions, the molecular packing in the crystal is also stabilized by intermolecular C-H···O interactions (Table 1, Fig. 2). Experimental 1.0 mol of 4-(benzyloxy) aniline (1.0 g) and 1.0 mol of ethyl 2-chloro-4-oxo-4,5-dihydrofuran-3-carboxylate (0.9 g) was allowed to stir in 10 ml of dichloromethane which contains 0.5 ml of triethylamine at room temperature for about 8 hrs.
The completion of the reaction was monitored by TLC. After the completion of reaction the crude solid was filtered and then recrystallized in ethanol.

Refinement
H atoms were positioned geometrically and were treated as riding on their parent C atoms, with aromatic C-H distances of 0.93 Å, methyl C-H distances of 0.96 Å and methylene C-H distances of 0.97 Å, and with U iso (H) = 1.5U eq (C) for methyl H and 1.2U eq (C) for other H atoms.  Atomic displacement parameters (Å 2 ) 0.0359 (7) 0.0384 (7 (7)