Diethyl Oxalate → HCID 135848643, compound

Participants

Reaction Steps

Diethyl oxalate (5.66 g, 38.7 mmol) and ethyl benzyloxyacetate (7.52 g, 38.7 mmol) in dry tetrahydrofuran (60 ml) were treated at 22° C. with sodium hydride (1.70 g of a 60% dispersion in mineral oil, 42.5 mmol) and the condensation product was reacted with a mixture of intermediate 11, 2-(2-(methylthio)ethoxy)propanamidine hydrochloride salt, (7.70 g, 38.7 mmol) in a solution of sodium ethoxide (19.3 mmol, prepared from 0.445 g of sodium) in ethanol (50 ml) to give 2.29 g (15% yield) of the title ester as a clear oil after chromatography on silica gel. 1HNMR 400 MHz (CDCl3) δ ppm: 1.33 (3H, t, J=7.1 Hz, CH3), 1.54 (3H, d, J=7.1 Hz, CH3), 2.16 (3H, s, SCH3), 2.7–2.8 (2H, m, CH2), 3.54 (1H, m, CH), 3.86 (1H, m, CH), 4.37 (2H, q, J=7.1 Hz, OCH2), 4.47 (1H, q, J=7.1 Hz, OCH), 5.34 (2H, ABq, JAB=11.0 Hz, OCH2), 7.37 (3H, m, aromatics), 7.49 (2H, m, aromatics). MS (ESI+) m/z 393 [M+H+].

Provenance & Evidence