Multi-step reaction with 11 steps
1: H2 / 10percent Pd/C / 760 Torr / Ambient temperature
2: 95 percent / triethylamine / CH2Cl2 / 0.5 h / 10 - 15 °C
3: 84.6 percent / Dowex50W-8x ion-exchange resin (H+ form / aq. ethanol / 1.5 h / Heating
4: 264 g / benzoic acid / 0.5 h
5: 268 g / trimethylchlorosilane / CH2Cl2 / 0.75 h / Heating
6: 182 g / aq. NaOH / methanol / 0.5 h / 15 °C
7: 92 percent / Na, MeOH / 16 h / Heating
8: POCl3 / toluene / 1.5 h / Ambient temperature
9: sodium bis(2-methoxyethoxy)aluminum hydride / toluene / 1.5 h / 80 °C
10: 92.3 percent / H2 / 10percent Pd/C / methanol / 0.67 h / 760 Torr / Ambient temperature
11: 4.0 N NaOH / dimethylsulfoxide / 2 h / 75 °C
With
methanol; sodium hydroxide; chloro-trimethyl-silane; Dowex50W-8x ion-exchange resin (H+ form; hydrogen; sodium; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; benzoic acid; trichlorophosphate;
palladium on activated charcoal;
In
methanol; ethanol; dichloromethane; dimethyl sulfoxide; toluene;
DOI:10.1021/jm00365a004