Hexane → a-(2-Thiazolyl)-3-((tert-butyldimethylsilyl)oxy)benzyl alcohol

Participants

Reaction Conditions

Reaction Steps

A solution of 1.6M n-butyllithium in hexane (206 mL, 0.33 mol) was cooled to -45° C. under nitrogen. A slurry of 2-bromothiazole (50 g, 0.30 mol) in 75 mL of diethyl ether was added in portions, maintaining a temp between -35° C. and -45° C. The resulting dark brown solution was stirred an additional 15 minutes at -40° C. before adding 3-(tert-butyldimethylsilyloxy)benzaldehyde (70.9 g, 0.30 mol, Example 54, infra) dropwise via syringe at a rate to maintain temperature between -25° C. and -35° C. The resulting mixture was stirred an additional 30 minutes at -15° C., then poured into a mixture of 1 L ice/600 mL 1M HCl. The organic phase was dried over sodium sulfate, and evaporated to give a brown oil. Chromatography on silica gel with hexane:ethyl acetate (gradient from 90:10 to 80:20) gave 25.5 g (26.4%) of a-(2-thiazolyl)-3-((tert-butyldimethylsilyl)oxy)benzyl alcohol as a viscous yellow oil.

Provenance & Evidence