Multi-step reaction with 8 steps
1: 99 percent / 3 h / 210 °C
2: 1.) O3, MeOH, 2,) PPh3 / 1.) CH2Cl2, -76 deg C, 30 min, 2.) CH2Cl2, MeOH, -76 deg C, 30 min
3: 89 percent / benzene / 28.5 h / Heating
4: 1.) NaH / 1.) THF, 0 deg C, 40 min, 2.) THF, a) 0 deg C, 15 min, b) 25 deg C, 25 h
5: 91 percent / NaBH4 / methanol / 4.5 h
6: 85 percent / N,N-diisopropylethylamine, CBr4, Ph3P / CH2Cl2 / 19 h
7: 1.) NaH / 1.) DMF, 15 min, 2.) DMF, 18 h
8: 81 percent / Na(Hg), NaH2PO4 / methanol / 5.25 h / 0 °C
With
methanol; sodium tetrahydroborate; sodium dihydrogenphosphate; sodium amalgam; carbon tetrabromide; sodium hydride; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine;
In
methanol; dichloromethane; benzene;
DOI:10.1021/jm9501339