Tributyltin Chloride → 3-Cyclopropyl-5-(tributylstannyl)isothiazole

Participants

Reaction Conditions

Reaction Steps

To a cold (−78° C.) solution of 3-cyclopropyl-5-iodoisothiazole (100 mg, 0.398 mmol) in anhydrous THF (2.0 mL) was added n-butyllithium (0.299 mL, 0.478 mmol) dropwise. The reaction mixture was stirred for 60 minutes at −78° C. A solution of tributylchlorostannane (0.129 mL, 0.478 mmol) in anhydrous THF (2.0 mL) was added to the reaction mixture, which was stirred for 30 minutes −78° C. and subsequently allowed to warm to ambient temperature over a 1 hour period. Saturated aqueous sodium bicarbonate was added to the reaction mixture. The aqueous phase was extracted with EtOAc and the combined organic phase was dried over anhydrous sodium sulfate, filtered, and evaporated in vacuo. The residue was purified by silica gel chromatography (Flash 60 column) eluting with hexane/EtOAc (19:1) to give the title compound as a colorless oil (142.8 mg, 87%). 1H NMR (500 MHz, CDCl3) δ ppm 0.85-0.93 (m, 9H), 0.95-1.05 (m, 4H), 1.09-1.17 (m, 6H), 1.28-1.38 (m, 6H), 1.47-1.61 (m, 6H), 2.20-2.29 (m, 1H), 6.93 (s, 1H).

Provenance & Evidence