Benzyl Bromide → HCID 11683652, compound

Participants

Reaction Conditions

Reaction Steps

6-O-tert-butyldimethylsilyl-D-glucal (11.5 mmol) was dissolved in dichloromethane (30 mL). Sodium hydroxide (23 mmol) followed by tetrabutylammonium bromide (5 mg) and benzyl bromide (27 mmol) were added and the reaction mixture was stirred at 40° C. After reaction was completed the reaction mixture was cooled down, solids were filtered off, filtrate was diluted with dichloromethane (100 mL), washed with water until neutral and dried over anhydrous sodium sulfate. Drying agent and solvents were removed and product was separated using column chromatography (SilicaGel 60) and hexanes:ethyl acetate as eluents. 3,4-di-O-benzyl-6-O-tert-butyldimethylsilyl-D-glucal (6.9 mmol, yield 60%) was obtained. [α]D−6.6 (c=1, chloroform).

Provenance & Evidence