Multi-step reaction with 12 steps
1: 91 percent / dimethylsulfoxide / 25 h / 23 °C
2: 86 percent / LDA / tetrahydrofuran; cyclohexane / 1.) -78 deg C, 30 min, then 30 min, 2.) -78 deg C, 2 h
3: 66 percent / LiBH4 / CH2Cl2 / 4 h / 23 °C
4: 67 percent / LAH / diethyl ether / 1.) 0 deg C, 1 h, 2.) r.t., 3.5 h
5: 83 percent / methanol / 24 h / 23 °C
6: 99 percent / CH2Cl2 / 3.75 h / 23 °C
7: 77 percent / LAH / diethyl ether / 1.5 h / 0 °C
8: 85 percent / CH2Cl2 / 0.83 h / 23 °C
9: 68 percent / N-chlorosuccinimide, dimethyl sulfide / toluene / 3.5 h / -25 - -20 °C
10: Na2SO4 / ethanol / 20.5 h / 23 °C
11: NaBH4 / ethanol / 10 h / 23 °C
12: 88 percent / CH2Cl2 / 11.5 h / 23 °C
With
sodium tetrahydroborate; N-chloro-succinimide; lithium aluminium tetrahydride; lithium borohydride; dimethylsulfide; sodium sulfate; lithium diisopropyl amide;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; cyclohexane; dimethyl sulfoxide; toluene;
DOI:10.1021/jo00076a017