Multi-step reaction with 9 steps
1: 1.) DIBAH / 1.) toluene, -78 deg C, 1.5 h, 2.) toluene, benzene, 70 deg C, 2 h
2: 94 percent / imidazole, 4-dimethylaminopyridine / CH2Cl2 / 2.5 h / Ambient temperature
3: H2 / 10percent Pd/C / ethanol / 11 h / Ambient temperature
4: DIBAH / CH2Cl2; hexane; 1,2-dimethoxy-ethane / 0.25 h / -78 °C
5: 87 percent / benzene / 1 h / Heating
6: 97 percent / DIBAH / toluene; hexane / 0.33 h / -78 °C
7: 96 percent / pyridinium dichromate / CH2Cl2 / 2 h / Ambient temperature
8: 82 percent / diethyl ether; tetrahydrofuran / 2.5 h / Ambient temperature
9: 95 percent / pyridine / 1 h / Ambient temperature
With
pyridine; 1H-imidazole; dmap; dipyridinium dichromate; hydrogen; diisobutylaluminium hydride;
palladium on activated charcoal;
In
tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; ethanol; hexane; dichloromethane; toluene; benzene;