Ethyl Acetate → HCID 69199559, compound

Participants

Reaction Steps

To a stirred solution of the product from Step A (3.5 g, 19.8 mmol) in methanol (30 mL) was added a sodium methoxide solution in methanol (25%, 9.2 ml, 29.3 mmol) at room temperature. After 30 min, (R)-propylene oxide (2.8 mL, 39.6 mmol) was added, and the resultant solution stirred for 3 h. The solution was diluted with saturated aqueous solution of ammonium chloride (20 mL) and extracted with ethyl acetate (3×65 mL). The combined extract was washed with brine (10 mL), dried (MgSO4) and evaporated to give a residue which was subjected to chromatography (silica, 30% ethyl acetate in hexane to 50% ethyl acetate in hexane) to give an oil (1.8 g, 39%): MS (ES) m/z 235 (M+); 1H NMR (CDCl3) 8.20 (1H, s), 8.07 (1H, s), 7.84 1H, d, J=7.2 Hz), 7.81 (1H, d, J=7.2 Hz), 4.47 (2H, dd, J=7.2 Hz), 4.34 (2H, m), 3.20 (1H, m), 1.44 (3H, t, J=7.2 Hz). 1.31 (3H, d, J=6.4 Hz).

Provenance & Evidence