Multi-step reaction with 9 steps
1: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 1 h, 2.) from -78 deg C to RT
2: 94 percent / ethyl chloroformate / CHCl3 / 0.25 h / 0 °C
3: 88 percent / dimethylformamide / 4 h
4: concd H2SO4, H2 / PtO2 / ethanol / 12 h / 2585.7 Torr
5: benzene / 3 h / Heating
6: 93 percent / LiAlH4 / tetrahydrofuran / 5 h / Heating
7: CH2Cl2; pyridine / 16 h / 0 - 25 °C
8: 1.) t-BuLi / 1.) THF, -70 deg C, 30 min, 2.) THF, from -70 deg C to 0 deg C, 20 min
9: 50 percent / 3percent Na/Hg / methanol / 30 h
With
sodium amalgam; lithium aluminium tetrahydride; n-butyllithium; sulfuric acid; hydrogen; tert.-butyl lithium; chloroformic acid ethyl ester;
platinum(IV) oxide;
In
tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00134a025