Tributyltin Chloride → HCID 67003585, compound

Participants

Reaction Conditions

Reaction Steps

To a cold (−78° C.) solution of the 2-(1-(methoxymethoxy)cyclobutyl)thiazole (Example 1B) (5.67 g, 28.5 mmol) in tetrahydrofuran (95 mL) was added a solution of lithium diisopropylamide (34.1 mmol) in tetrahydrofuran (30 mL) dropwise. The solution was stirred at −78° C. for 45 minutes, and tributyltin chloride (9.26 mL, 34.1 mmol) was added dropwise. The cold bath was removed, and the reaction warmed to room temperature. The ambient reaction was then quenched by the addition of saturated aqueous ammonium chloride solution and ether. The layers were separated, and the aqueous layer was extracted with additional ether. The combined organics were washed with water, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the title compound, which was used without further purification. MS ESI(+) m/z 490 [M+H]+.

Provenance & Evidence