Thionyl Chloride → HCID 118208875, compound

Participants

Reaction Steps

Thionyl chloride (5.07 ml, 69.4 mmol) was added to a mixture of (4R,5R)-4-(hydroxymethyl)-5-methyloxazolidin-2-one (1.82 g, 13.88 mmol) in pyridine (35 mL) at 0° C. and the mixture was allowed to warm to room temperature for one hour. The mixture was then heated to 60° C. for one hour, allowed to cool to room temperature and then concentrated under reduced pressure. The crude oil was purified by column chromatography on silica to afford (4S,5R)-4-(chloromethyl)-5-methyloxazolidin-2-one. 1H NMR (500 MHz, CDCl3) δ 6.23 (s, 1H), 4.50 (qd, J=6.3, 4.6 Hz, 1H), 3.74-3.63 (m, 1H), 3.59-3.48 (m, 2H), 1.48 (d, J=6.4 Hz, 3H).

Provenance & Evidence