Multi-step reaction with 10 steps
1: NaH / tetrahydrofuran; dimethylformamide / Ambient temperature
2: 1N HCl / 1,2-dimethoxy-ethane / Ambient temperature
3: Jones reagent / acetone / 0 °C
4: 1) LDA / 2) THF, HMPA, -78 deg C
5: Et3N / CH2Cl2 / -10 °C
6: DBU / benzene / 50 °C
7: 1) Et2O, CH2Cl2, 0 deg C 2) irradiation, benzophenone, -70 deg C, PhCH3
8: 83 percent / LiAlH4 / diethyl ether / -10 °C
9: imidazole / dimethylformamide / Ambient temperature
10: i-Pr2NEt / 1,2-dichloro-ethane / 50 °C
With
1H-imidazole; hydrogenchloride; lithium aluminium tetrahydride; jones reagent; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide;
In
tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1016/0040-4039(90)80020-M