Multi-step reaction with 8 steps
1: 77 percent / p-TsOH*H2O, 4A molecular sieves / benzene / Ambient temperature
2: Et3N / CH2Cl2 / 1.) -78 deg C, 90 min, 2.) 0 deg C, 60 min
3: toluene / 76 h / Heating
4: 1 N HCl / toluene; tetrahydrofuran / 3 h / Ambient temperature
5: diethyl ether; ethyl acetate
6: 1.) a) BH3, 2.) 30percent H2O2, 3 N NaOH / 1.) a) THF, -78 deg C, 30 min, b) 0 deg C, 90 min, 2.) THF, RT, 3 h
7: 100 percent / Et3N / CH2Cl2 / 1 h / 0 - 20 °C
8: LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C
With
hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; 4 A molecular sieve; borane; dihydrogen peroxide; toluene-4-sulfonic acid; triethylamine;
In
tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; toluene; benzene;
DOI:10.1021/ja00170a024