Sodium borohydride → HCID 18367371, compound

Participants

Reaction Steps

NaBH4 (119 mg) was added to a stirred solution of ethyl 3-[3-(tert-butyldiphenylsilyloxy)benzyl]-4- (4,5-diphenyl-2-oxazolyl)-4-oxobutyrate (430 mg) in methanol (2.0 ml) and 1,2-dimethoxyethane (0.5 ml) at room temperature and the resulting mixture was stirred at the same temperature for 3 hours. The reaction mixture was partitioned between ethyl acetate -1N hydrochloric acid. The organic layer was washed with 1N hydrochloric acid, aqueous sodium bicarbonate, and brine, dried over MgSO4, and evaporated in vacuo. The residue was chromatographed over silica gel to afford 3-[3-(tert-butyldiphenylsilyloxy)benzyl]-2- (4,5-diphenyl-2-oxazolyl)-5-oxotetrahydrofuran (366 mg) as an amorphous powder. NMR (CDCl3, δ): 1.08 and 1.09 (9H, each s), 1.40-1.62 (1H, m), 2.31-2.97 (2H, m), 3.48-3.88 (2H, m), 4.58 and 4.80 (1H, each m), 6.54-7.05 (2H, m), 7.32-7.73 (22H, m)

Provenance & Evidence