Multi-step reaction with 11 steps
1: 77 percent / diisopropylamine / CH2Cl2 / 6 h
2: 83 percent / LiAlH4 / diethyl ether / 1 h / Ambient temperature
3: imidazole / dimethylformamide / 24 h
4: 62 percent / p-TsOH*H2O / acetone / 0.25 h / Heating
5: 85 percent / NaBH4 / dioxane / 1 h
6: 70 percent / NaH / tetrahydrofuran / 1.) 1 h, 2.) reflux, 20 h
7: 77 percent / ZnBr2 / CH2Cl2 / 7 h
8: 78 percent / NaH / tetrahydrofuran / 1.) 1 h, 2.) reflux, 20 h
9: 92 percent / Bu4NF / tetrahydrofuran / 48 h
10: 96 percent / NaH / tetrahydrofuran / 1.) 1 h, 2.) reflux, 20 h
11: 76 percent / B-chlorocatecholborane / CH2Cl2 / 0.5 h
With
1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; 2-chloro-1,3,2-benzodioxaborole; tetrabutyl ammonium fluoride; sodium hydride; toluene-4-sulfonic acid; diisopropylamine; zinc dibromide;
In
tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo00094a044