Tributyltin Chloride → 2-Methyl-5-(tributylstannyl)thiazole

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To a cold (−78° C.) solution of 2-methylthiazole (2.80 g, 28.2 mmol) in anhydrous THF (100 mL) was added butyllithium (19.41 mL, 31.1 mmol) dropwise. After stirring for 60 min at −78° C., a solution of tributylchlorostannane (9.14 mL, 33.9 mmol) in anhydrous THF was added to the reaction mixture. The reaction mixture was stirred for 30 min at −78° C. and then allowed to warm to RT over a 2 to 3 h period. Saturated aq NaHCO3 was added and the aqueous phase was extracted with ether (3×200 mL). The combined organic phase was dried over anhydrous Na2SO4, filtered, and evaporated in vacuo. The crude product was purified on a silica gel column eluting with 10-50% EtOAc in Hexane over a 60 min period. The fractions were collected and solvent was removed in vacuo to give the title compound as a yellow oil (72%). 1H NMR (500 MHz, DMSO-d6) δ ppm 0.71-0.92 (m, 9 H), 0.96-1.18 (m, 6 H), 1.23-1.38 (m, 6 H), 1.40-1.64 (m, 6 H), 2.69 (s, 3 H), 7.56 (d, J=12.69 Hz, 1 H).

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