Multi-step reaction with 6 steps
1: 1.) n-BuLi / 1) hexane, Et2O, -78 deg C, 4 h; 2) Et2O, hexane, -85 deg C, 2 h
2: 1.) n-BuLi / 1) hexane, Et2O, -78 deg C, 15 min; 2) hexane, Et2O, 3 h
3: 1.) CuCN, LiCl / 1) THF, -78 deg C; 2) THF, -78 deg C, 6 h, -78 deg C --> rt, 12 h
4: tetrabutylammonium fluoride / tetrahydrofuran / 1) rt, 8 d; 2) 60 deg C, 20 h
5: 98 percent / pyridinium dichromate, pyridinium tosylate / CH2Cl2 / 5 h / Ambient temperature
6: 1.) PhLi / 1) cyclohexane, Et2O, THF, -78 deg C, 10 min; 2) cyclohexane, Et2O, THF, -78 deg C, 3 h, -65 deg C, 30 min
With
dipyridinium dichromate; n-butyllithium; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; phenyllithium; lithium chloride;
In
tetrahydrofuran; dichloromethane;
DOI:10.1021/jo970604u