Multi-step reaction with 9 steps
1: 2 h / 90 °C
2: 18 percent / phosphorus oxychloride / toluene / 4 h / Heating
3: 78 percent / LiAlH4 / diethyl ether / 1 h / Ambient temperature
4: 35 percent / carbon tetrabromide, triphenylphosphine / diethyl ether / 1.) 0 deg C, 10 min, 2.) RT, 3 h
5: 1.) sodium hydride / 1.) THF, 15 min, 2.) THF, a) 0 deg C, 1 h, b) RT, 2 h
6: n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, DMF, -78 deg C, 1 h
7: 49 percent / piperidine / ethanol / 24 h / Heating
8: 57 percent / 3percent sodium amalgam / methanol / 20 h
9: 47 percent / m-CPBA / CH2Cl2 / 2 h / Ambient temperature
With
piperidine; sodium amalgam; lithium aluminium tetrahydride; n-butyllithium; carbon tetrabromide; sodium hydride; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; trichlorophosphate;
In
methanol; diethyl ether; ethanol; dichloromethane; toluene;
DOI:10.1021/jm00088a022