Multi-step reaction with 8 steps
1: 98 percent / 4-dimethylaminopyridine / acetonitrile; triethylamine / 3 h / Ambient temperature
2: diisobutylaluminium hydride / hexane; tetrahydrofuran / -78 deg C, 1 h, then 0 deg C, 2 h
3: pyridinium p-toluenesulfonate / 12 h / Ambient temperature
4: NaH / paraffin; dimethylformamide / 1 h / Ambient temperature
5: 68 percent / boron trifluoride etherate / CH2Cl2 / 1 h / -78 °C
6: 62 percent / diisobutylaluminium hydride / toluene / 1 h / -78 °C
7: 1.) potassium carbonate; 2.) sodium borohydride / 1.) methanol, reflux, 2 h; 2.) methanol, room temp., 30 min
8: 99 percent / dimethyl sulfoxide, oxalyl chloride / CH2Cl2 / 0.25 h / -78 °C
With
dmap; sodium tetrahydroborate; oxalyl dichloride; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide;
In
tetrahydrofuran; hexane; dichloromethane; triethylamine; N,N-dimethyl-formamide; toluene; acetonitrile; paraffin;
DOI:10.1016/S0040-4020(01)80643-8