Multi-step reaction with 5 steps
1: 67 percent / iPr2NEt, Pd(PPh3)4 / dimethylformamide / Ambient temperature
2: 1.) Me3Al / 1.) hexane, toluene, from 0 deg C to RT, 55 min, 2.) hexane, toluene, a) RT, 4 h, b) 60 deg C, 2 h
3: NaH / tetrahydrofuran / 3 h / Ambient temperature
4: n-Bu4NBr, 1M aq. NaOH / CH2Cl2 / 12 h / Ambient temperature
5: 1.) NaH / 1.) THF, from 0 deg C to RT, 3 h, 2.) THF, RT, overnight
With
sodium hydroxide; tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; trimethylaluminum; sodium hydride; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja980787h