2-Bromothiazole → tert-butyl N-[4-oxo-4-(1,3-thiazol-2-yl)butyl]carbamate

Participants

Reaction Conditions

Reaction Steps

A solution of 2-bromothiazole (3.6 g) in dry tetrahydrofuran (100 ml) was cooled to −78° C. under an atmosphere of nitrogen. A 2.5M solution of n-butyllithium in hexane (8.8 ml) was added dropwise over 15 minutes maintaining the temperature below −60° C. The product from step (a) (2.46 g) in tetrahydrofuran (20 ml) was then added over 15 minutes again keeping the temperature below −60° C. The reaction mixture was then maintained at −70° C. for 1 h, then allowed to warm to −10° C. over 1.5 h. The reaction mixture was then partitioned between 10% ammonium chloride solution and ethyl acetate and the resulting colloid was filtered through celite. The organic extracts were dried over magnesium sulfate, filtered and the filtrate evaporated. The resulting dark brown oil was purified by flash chromatography, eluting with hexane:ethyl acetate (2:1) to give the subtitle compound as a pale yellow oil (0.9 g, 15%).

Provenance & Evidence