ammonium chloride in tetrahydrofuran; methanol; water To a stirred soln. of Me3SnCu*Me2S in THF (Ar, -78°C) was added sequentially a THF soln. of the 1-alkyne and CH3OH. The mixt. was stirred(10 min) and then at -63°C (12 h). Satd. aq. NH4Cl and ether were added; allowed to warm to room temp.; Aq. phase was extd. with ether. The org. exts. were washed (satd. aq. NH4Cl) and dried (MgSO4). Removal of the solvent; column chromy. (silica gel) followed by distillation. (E)-1-trimethylstannyl-1-alkene not isolated, detected by gas-liq. chromy..;

methanol in tetrahydrofuran molar ratio Sn:alkyne:MeOH=1:2:60; chromy. (SiO2, light petroleum);