Tributyltin Chloride → HCID 71143893, compound

Participants

Reaction Conditions

Reaction Steps

To a cold (−78° C.) mixture of 1,3-dimethyl-1H-thieno[2,3-c]pyrazole (1.0 g, 6.57 mmol) and THF (50 mL) was added n-butyllithium (4.52 mL, 7.23 mmol) dropwise and allowed under a nitrogen atmosphere. The reaction mixture was stirred at −78° C. for 1 hour. To this solution was added tributylchlorostannane (2.13 mL, 7.88 mmol) and the mixture was stirred at −78° C. for 1 hour and then warmed to room temperature over a period of 2 hours. The reaction was quenched with brine (100 mL) and extracted with ethyl acetate (2×100 mL). The organic layers were combined, dried over sodium sulfate, concentrated, and purified via silica gel flash chromatography, eluting with 20% EtOAc and hexane to give the title compound as a clear oil (1.60 g, 55%). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.86 (t, J=7.33 Hz, 9H), 1.02-1.06 (m, 6H), 1.30 (dq, J=7.29, 14.75 Hz, 6H), 1.44-1.64 (m, 6H), 2.31 (s, 3H), 3.80 (s, 3H), 6.94 (s, 1H).

Provenance & Evidence