Multi-step reaction with 9 steps
1: N-bromosuccinimide, benzoyl peroxide / CCl4 / 3 h / Heating
2: NEt3 / tetrahydrofuran / 1.5 h / 0 °C
3: 82 percent / LiAlH4 / diethyl ether / 2 h / 0 °C
4: 1) n-BuLi / 1) THF, hexane, -78 deg C, 15 min, 2a) -78 deg C, 5 min, b) to r.t.
5: 89 percent / n-Bu3SnH, AIBN / benzene / 2.5 h / Heating
6: 1) Me2S*BH3, 2) 3 N NaOH, H2O2 / 1) THF, Et2O, -20 deg C, 2) MeOH
7: activated MnO2 / CHCl3
8: tetrahydrofuran / Ambient temperature
9: 4 Angstroem molecular sieves, VO(acac)2, t-BuOOH / CH2Cl2 / -20 °C
With
tert.-butylhydroperoxide; manganese(IV) oxide; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; Perbenzoic acid; bis(acetylacetonate)oxovanadium; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; 4 A molecular sieve; dihydrogen peroxide; tri-n-butyl-tin hydride; triethylamine;
In
tetrahydrofuran; tetrachloromethane; diethyl ether; dichloromethane; chloroform; benzene;
DOI:10.1021/jo00029a033