Propylene Oxide → HCID 22285728, compound

Participants

Reaction Steps

To a solution of the product from Step B (4.85 g, 23.9 mmol) in ethanol (50 mL) was added sodium ethoxide (14.2 mL, 35.0 mmol, 21% solution in ethanol) at room temperature. After 30 min, propylene oxide (4.14 mL, 47.8 mmol) was added, and the resultant solution was stirred for 18 h at room temperature. A saturated aqueous ammonium chloride solution (20 mL) was added to the reaction mixture and the ethanol was evaporated. This mixture was extracted with ethyl acetate (3×65 mL) and the combined extracts were washed with brine (30 mL), dried (MgSO4), and evaporated. The residue was purified by column chromatography (silica, 50% to 80% gradient of ethyl acetate in hexane) to yield the desired product as a solid (2.0 g, 32%): m.p: 147-148° C.; MS (ES) m/z 262 (M+); 1H NMR (CDCl3) δ 8.17 (1H, s), 7.74 (1H, s), 4.31 (3H, m), 3.05 (4H, 2d, J=6.0 Hz), 2.19 (4H, m), 1.30 (3H, t, J=6.0 Hz). The regioisomer formed during the alkylation was also isolated as a solid (1.4 g, 22%): mp 140-141° C.

Provenance & Evidence