Multi-step reaction with 16 steps
1: 1.) NaBH3CN, methanolic HCl, 2.) CH3COONa*3H2O / 1.) THF, 2 h, 2.) C2H5OH, reflux, 2 h
2: 95 percent / diisobutylaluminum hydride / CH2Cl2; toluene / 0.25 h / -78 °C
3: 93 percent / 2 h / 95 °C
4: 93 percent / imidazole / dimethylformamide / 0.5 h
5: 86 percent / aq. (CH3COO)2Cu / tetrahydrofuran / 36 h / 70 °C
6: 1.) NaH / 1.) C6H6, 5 min, 2.) C6H6, reflux, 45 min
7: 96 percent / aq. H2SO4 / ethanol / 3 h / Ambient temperature
8: 83 percent / Celite, pyridinium dichromate / CH2Cl2 / 17 h
9: 68 percent / 4-(dimethylamino)pyridine, Et3N / tetrahydrofuran / 48 h / 55 °C
10: 98 percent / H2 / 5percent Pt/C / benzene / 0.5 h / 10343 Torr
11: 100 percent / EtONa / ethanol / 1 h
12: 93 percent / pyridine / 2 h
13: 93 percent / NaI / acetone / 36 h / Heating
14: 84 percent / dimethylsulfoxide / 8 h
15: 74 percent / t-BuOK / benzene / 0.33 h / Heating
16: 1.) NaH / 1.) DMF, 5 min, 2.) DMF, 1 h
With
pyridine; 1H-imidazole; hydrogenchloride; dmap; dipyridinium dichromate; Celite; sulfuric acid; potassium tert-butylate; hydrogen; sodium ethanolate; copper diacetate; sodium acetate; sodium hydride; diisobutylaluminium hydride; sodium cyanoborohydride; triethylamine; sodium iodide;
platinum on activated charcoal;
In
tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; benzene;
DOI:10.1021/jo00350a063