Ethylene Oxide → HCID 67273922, compound

Participants

Reaction Steps

A solution of 2-bromo-3-methylthiophene (35.4 g, 200 mmol, ALFA) in diethyl ether (200 mL) was added drop wise to Mg turnings (5.35 g, 220 mmol) over ˜30 min at such a rate as to maintain gentle reflux (at the beginning the reaction was initiated with 2 drops of Br2). After refluxing for 1 h, 2.0M ethylene oxide in THF (150 mL, 300 mmol) was added drop wise at 0° C. over 1 h and stirring was continued at rt for 20 h. After cooling to 0° C. acetyl chloride (22.8 mL, 320 mmol) was added drop wise at 0° C. over 15 min an the suspension was stirred at rt for 18 h. The reaction mixture was diluted with diethyl ether (200 mL) and washed with 1M HCl (200 mL) and 10% brine (200 mL). The aqueous layers were extracted with diethyl ether (100 mL) and the combined organic layers were dried (Na2SO4) and evaporated affording 49 g brownish oil which was purified by distillation affording 32.8 g (89.0%, GC 96.4%) colorless oil, bp ˜120° C./10 mbar.

Provenance & Evidence