Thiazole → HCID 67003630, compound

Participants

Reaction Conditions

Reaction Steps

To a cold (−78° C.) solution of thiazole (1.0 mL, 14.1 mmol) in tetrahydrofuran (70 mL) was added n-butyllithium (11.83 mL, 14.1 mmol, 2.38 M in hexane) dropwise. After 15 minutes, cyclobutanone (1.06 mL, 14.1 mmol) was added in a single portion. The reaction was stirred at −78° C. for 30 minutes, and n-butyllithium (11.83 mL, 14.1 mmol, 2.38 M in hexane) was added dropwise. The reaction was stirred for an additional 20 minutes, after which tributyltin chloride (3.82 mL, 14.1 mmol) was added dropwise. After 10 minutes, the cold reaction was quenched by the addition of saturated aqueous ammonium chloride solution (100 mL) and ethyl acetate (100 mL). The reaction was warmed to ambient temperature. The layers were separated, and the aqueous layer was extracted with additional ethyl acetate (2×100 mL). The combined organics were dried with anhydrous Na2SO4, filtered, and concentrated. Trituration of the residue with hexane gave the title compound, which was used without further purification. MS ESI(+) m/z 445.3 [M+H]+.

Provenance & Evidence