Tributyltin Chloride → cis-1-Ethoxy-2-(tri-n-butylstannyl)ethylene

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(Ref. Wollenberg, R. H.; Albizati, K. F.; Peries, R. J. Am. Chem. Soc. 1977, 99, 22, 7365-7367.) To a −78° C. solution of (Z)-2-ethoxy-1-bromoethene (5.0 mL, 46.8 mmol) in diethyl ether (160 mL) was added a 1.7 M solution of tert-butyl lithium in pentane (55 mL), dropwise over 20 min. This pale yellow solution was stirred at −78° C. for 40 min, and then chloro-tri-n-butylstannane (13.3 mL, 49.0 mmol) was added, dropwise over 7 minutes. The resulting reaction mixture was allowed to warm slowly. Once the cooling bath had reached −30° C., saturated aq. NaHCO3 (150 mL) was added, and the cooling bath was removed. This mixture was stirred for 15 minutes, and then the layers were separated. The aq. layer was extracted with diethyl ether (2×50 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated to afford (Z)-2-ethoxy-1-tri-n-butylstannanylethene.

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