Water → HCID 68559484, compound

Participants

Reaction Steps

To a solution of (2-bromophenyl)methanol (4.4 g) in dry tetrahydrofuran (90 mL) was added n-butyllithium (1.6 M hexane solution, 31 mL) at −78° C., and the mixture was warmed to room temperature over 2 hr. A solution of tert-butyl 3-oxoazetidine-1-carboxylate (4.0 g) in dry tetrahydrofuran (30 mL) was added at −78° C., and the mixture was stirred at room temperature for 18 hr. The reaction solution was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (50% ethyl acetate/hexane to 60% ethyl acetate/hexane) to give the object product (4.0 g, 61%).

Provenance & Evidence