Multi-step reaction with 9 steps
1: 77 percent / 1.) lithium diisopropylamide / tetrahydrofuran / 1.) -78 deg C, 0.5 h, 2.) r.t., 2 h
2: 95 percent / LiAlH4 / diethyl ether / 2 h
3: 73 percent / diisopropyl azodicarboxylate, triphenylphosphine / tetrahydrofuran / 14 h / Ambient temperature
4: 88 percent / NaBH4 / methanol / 4 h
5: 63 percent / n-Bu3P / benzene / 24 h / Ambient temperature
6: 57 percent / tri-n-butyltin hydride, azobisisobutyronitrile / benzene / 4 h / Heating
7: 1.) 10percent sodium hydroxide / 1.) ethanol, reflux, 10 h, 2.) ethanol, water, toluol, 0.5 h
8: 1.) oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 17 min, 2.) CH2Cl2, -78 deg C, 15 min, r.t., 5 min
9: 63 percent / tris(triphenylphosphine)rhodium chloride / benzene / 2 h / Heating
With
sodium hydroxide; sodium tetrahydroborate; Wilkinson's catalyst; lithium aluminium tetrahydride; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tributylphosphine; di-isopropyl azodicarboxylate; tri-n-butyl-tin hydride; triethylamine; triphenylphosphine; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; benzene;