Multi-step reaction with 8 steps
1: 65 percent / LiAlH4 / diethyl ether / 1.) 10 h, 2.) reflux, 1.5 h
2: 88 percent / NaH / tetrahydrofuran / 1.) r.t., 1 h, 2.) r.t., 8 h
3: 79 percent / Ph3P, diisopropyl azodicarboxylate / tetrahydrofuran / 1.) ice-cooling, 10 min, 2.) r.t. 12 h
4: 82 percent / NaBH4 / methanol / 1.) 0 deg C, 30 min, 2.) r.t., 2 h
5: 55 percent / Bu3P / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) r.t., 12 h
6: 87 percent / Amberlyst / methanol / 15 h / Heating
7: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) CH2Cl2, r.t., 2 h
8: 1.) BuLi / 1.) THF, hexane, -30 deg C, 0.5 h, 2.) 10 deg C, 5 h
With
sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; tributylphosphine; di-isopropyl azodicarboxylate; Amberlyst; sodium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine;
In
tetrahydrofuran; methanol; diethyl ether;
DOI:10.1039/a804666b