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. The mixt. was stirred (6h). CH3OH, satd. aq. NH4Cl and ether were added; allowed to warm to room temp.; The org. phase was washed (satd. aq. NH4Cl) and dried (MgSO4). Removal of the solvent; flash chromy. (silica gel) provided 3-tetrahydropyranyloxy-2-trimethylstannylpropene and (E)-3-tetrahydropyranyloxy-1-trimethylstannylpropene.;
参考文献
Canadian Journal of Chemistry, , vol. 66, p. 1425 - 1429
1: With n-butyllithium in tetrahydrofuran; N,N,N',N',N'',N''-hexamethylphosphoric triamide; hexane T=0 - 20°C; 2: With p-toluenesulfonic acid monohydrate in methanol T=20°C; Further stages.;
参考文献
Oppolzer; Radinov; El-Sayed
Journal of Organic Chemistry, 2001 , vol. 66, # 14 p. 4766 - 4770
methyl lithium LiBr complex; dimethyl sulfoxide 1.) 0 deg C, THF, ether, 15 min 2.) from 0 deg C to room temperature, stiring at room temperature 3h; Yield given. Multistep reaction. Yields of byproduct given;
参考文献
Chong, J. Michael; Wong, Susanna
Tetrahedron Letters, 1986 , vol. 27, # 45 p. 5445 - 5448
1: 1.) tributyltin hydride, dibenzoyl peroxide; 2.) BuLi / 1.) 90 deg C, 3 h; 2.) THF, -70 deg C, 1 h then -30 deg C, 2 h 2: p-TsOH / methanol; H2O / 6 h / Ambient temperature View Scheme
参考文献
Berg, Ellen M. M. van den; Liemt, Willem B. S. van; Heemskerk, Bram; Lugtenburg, Johan
Recueil des Travaux Chimiques des Pays-Bas, 1989 , vol. 108, # 9 p. 304 - 313
