Thiazole → 1-(1,3-Thiazol-2-yl)cyclobutan-1-ol

Participants

Reaction Steps

To a cold (−78° C.) solution of thiazole (6.59 ml, 93 mmol) in tetrahydrofuran (238 mL) was added n-butyllithium (58.0 mL, 93 mmol) dropwise. The reaction was stirred for 15 minutes, and cyclobutanone (5.0 g, 71.3 mmol) was added via syringe. The reaction was stirred for 10 minutes and was then quenched by the addition of saturated aqueous bicarbonate solution. The cold bath was removed, and the reaction was warmed to room temperature. Ethyl acetate was added, and the layers were separated. The aqueous layer was extracted with additional ethyl acetate (2×). The combined organics were dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the title compound, which was used in the subsequent step without further purification. MS ESI(+) m/z 156 [M+H]+.

Provenance & Evidence