Multi-step reaction with 8 steps
1: 93 percent / LiAlH4, AlCl3 / diethyl ether; tetrahydrofuran / 0.83 h / -5 °C
2: Et3N / CH2Cl2 / 0.67 h / -70 °C
3: 1.) Na, 2.) n-BuLi / 1.) CH2Cl2, EtOH, 0 deg C, 50 min; r.t., 50 min, 2.) hexane, THF
4: imidazole / CH2Cl2 / 2 h / Ambient temperature
5: 94.5 percent / potassium naphthalenide / tetrahydrofuran / 0.83 h / -78 °C
6: 1.) Et2BH, 2.) 10percent aq. NaOH, 35percent H2O2 / 1.) THF, 0 deg C, 30 min; r.t., 7 d, 2.) r.t., 3 h
7: 81 percent / CsF, EtOK / ethanol; tetrahydrofuran / 42 h / 65 °C
8: 95 percent / Dess-Martin periodinane / CH2Cl2 / 2 h / Ambient temperature
With
1H-imidazole; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; Diethylborane; potassium naphthalenide; potassium ethoxide; dihydrogen peroxide; sodium; Dess-Martin periodane; triethylamine; cesium fluoride;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane;
DOI:10.1055/s-1998-1599