Benzyl Bromide → HCID 89576927, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (3.18 g, 32.65 mmol, 60% dispersion in Mineral oil) in anhydrous tetrahydrofuran (15 mL) was added a solution of (2S,3R,4S,5S,6R)-6-[[tert-butyl (dimethyl)silyl]oxymethyl]-2-[4-chloro-3-[(4-ethoxy-2,3-difluoro-phenyl)methyl]phenyl]-2-methoxy-tetrahydropyran-3,4,5-triol 23h (11.16 g, 18.95 mmol) in anhydrous tetrahydrofuran (80 mL) slowly at 0° C. The mixture was stirred at 0° C. for 1 hour, and then benzyl bromide (20.3 mL, 170.55 mmol) was added. The mixture was warmed up to room temperature and tetrabutylammonium iodide (0.70 g, 1.90 mmol) was added. The mixture was stirred for 12 hours. The reaction mixture was quenched with water (100 mL) at 0° C. and extracted with ethyl acetate (100 mL×2). The combined organic layers were dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound 23i as yellow oil (36.90 g, 100%). This material was not further purified.

Provenance & Evidence