Tributyltin Chloride → HCID 67003527, compound

Participants

Reaction Conditions

Reaction Steps

To a cold (−78° C.) solution of the 2-(3-(4-methoxybenzyloxy)oxetan-3-yl)thiazole (Example 11D) (1.8 g, 6.49 mmol) in tetrahydrofuran (11 mL) was added a solution of lithium diisopropylamide (7.79 mmol in 10 mL tetrahydrofuran) dropwise. The solution was stirred at −78° C. for 45 minutes, and tributyltin chloride (2.11 mL, 7.79 mmol) was added dropwise. The cold bath was removed, and the reaction slowly warmed to room temperature. The ambient reaction was then quenched by the addition of saturated aqueous ammonium chloride solution and diethyl ether. The layers were separated, and the aqueous layer was extracted with additional diethyl 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 568.7 [M+H]+.

Provenance & Evidence