Multi-step reaction with 11 steps
1: Et3N / CH2Cl2 / 1.) -78 deg C, 90 min, 2.) 0 deg C, 60 min
2: toluene / 76 h / Heating
3: 1 N HCl / toluene; tetrahydrofuran / 3 h / Ambient temperature
4: diethyl ether; ethyl acetate
5: 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
6: 100 percent / Et3N / CH2Cl2 / 1 h / 0 - 20 °C
7: LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C
8: 89 percent / oxalyl chloride, DMSO / CH2Cl2 / 0.17 h / -78 °C
9: 1.) t-BuOK / 1.) THF, -78 deg C, 10 min, 2.) a) -78 deg C, 10 h, b) -20 deg C, 10 h
10: 1.) n-BuLi / 1.) THF, from -78 to -35 deg C, 2 h, 2.) from -78 deg C to RT, 14 h
11: 1.) Cp2ZrHCl, 2.) N-bromosuccinimide / 1.) benzene, 35-40 deg C, 70 min, 2.) RT, 25 min
With
hydrogenchloride; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; Schwartz's reagent; n-butyllithium; oxalyl dichloride; borane; potassium tert-butylate; dihydrogen peroxide; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; toluene;
DOI:10.1021/ja00170a024