Ethylene Oxide → HCID 13144701, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.6M BuLi in hexane (98.4 mL, 157.5 mmol) and THF (150 mL) was added at −78° C. a solution of 3-bromo-2-methyl-thiophene (CAS 30319-05-2, 26.6 g, 150 mmol) in THF (50 mL) and stirring at −78° C. was continued for 1 h. 2.0M ethylene oxide in THF (112.5 mL, 225 mmol) and then BF3-Et2O (20.4 mL, 165 mmol) was added dropwise at −70° C. and the yellow solution was stirred at −78° C. for 1 h. After warming to 0° C. the reaction mixture was quenched with 10% brine (400 mL) and extracted with ethyl acetate (400+200 mL). The organic layers were washed with 10% brine, dried (Na2SO4) and evaporated affording 18.6 g crude product as a yellow oil. Purification by chromatography over silica with hexane-ethyl acetate 5:1 gave 14.9 g (70%, GC 94.7%) yellow oil.

Provenance & Evidence