Diethyl Ether → 1-Methyl-4-(tributylstannyl)-1H-pyrazole

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromo-1-methylpyrazole (15 g, 38.5 mmol) in ether (150 mL) n-Butyllithium (2.5M in hexanes, 17 mL, 42.4 mmol) was added at −78° C. After the reaction solution was stirred at −78° C. for 30 minutes, tributyltin chloride (11.5 mL, 42.4 mmol) was added. It was stirred at −60° C. for 1 hour and warmed to room temperature, at which it was stirred for 1 more hour. Then, it was diluted with ethyl acetate (300 mL) and washed with water (200 mL) and brine. The organic layer was dried over anhydrous sodium sulfate and concentrated. The crude product was purified by flash column chromatography on silica gel with hexanes/ethyl acetate=10/1 as eluant to get 1-methyl-4-tributylstannylpyrazole as a white wax. 1H NMR (CDCl3, 300 MHz): δ7.42 (s, 1H), 7.23 (s, 1H), 3.93 (s, 3 H). 1.28-1.55 (m, 18 H), 0.91 (t, J=15 Hz, 9 H).

Provenance & Evidence