Multi-step reaction with 10 steps
1: LiAlH4 / tetrahydrofuran / 6 h / Heating
2: 1.) DMSO, oxalyl chloride, 2.) Et3N / 1.) CH2Cl2, -60 deg C, 2 min, 2.) CH2Cl2, 5 min
4: 82 percent / propionic acid / 3 h / 140 °C
5: LiAlH4 / diethyl ether / 2 h / Ambient temperature
6: Ph3P, CBr4 / diethyl ether / 8 h / Ambient temperature
7: 88 percent / DMSO / 2 h / 50 °C
8: 63 percent / DIBAL-H / benzene / 14 h / Ambient temperature
9: 97 percent / 1.92M t-BuLi / 1.) pentane, ether, -78 deg C, 45 min, 2.) ether, r.t., 8 h
10: 99 percent / n-Bu4NF / tetrahydrofuran / 8 h / Ambient temperature
With
lithium aluminium tetrahydride; oxalyl dichloride; carbon tetrabromide; tetrabutyl ammonium fluoride; tert.-butyl lithium; diisobutylaluminium hydride; dimethyl sulfoxide; propionic acid; triethylamine; triphenylphosphine;
In
tetrahydrofuran; diethyl ether; benzene;
DOI:10.1021/jo00079a045