Allyl bromide → HCID 22086396, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1-9 (19.3 g, 57.9 mmol) in tetrahydrofuran (400 mL) at −78° C. under argon was added a solution of lithium bis(trimethylsilylamide) (75.2 mL of a 1.0 M solution in tetrahydrofuran) over 20 min. After an additional 20 min., allyl bromide (14.0 g, 116 mmol) was added in one portion. After 20 min., the reaction mixture was allowed to warm to 0° C. After 3.5 h, the reaction mixture was diluted with ethyl acetate, washed with water, saturated aqueous sodium hydrogen carbonate, saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate. The reaction mixture was filtered and concentrated at reduced pressure. The resulting oil was purified by flash column chromatography (silica gel, 25 to 35% ethyl acetate/hexanes) to give 1-10 as an oil.

Provenance & Evidence