Multi-step reaction with 7 steps
1: pyridinium chlorochromate, sodium acetate / CH2Cl2 / 1.5 h
2: tetrahydrofuran; diethyl ether / -78 °C
3: 86 percent / pyridinium chlorochromate, sodium acetate / CH2Cl2 / 1.5 h
4: 52 percent / p-toluenesulfonic acid / 7 h / Heating
5: 1.) n-butyllithium / 1.) THF, hexane, -78 deg C 2.) THF, hexane, 0 deg C
6: 1.) n-butyllithium, HMPA / 1.)THF, hexane, -78 degC to 0 degC 2.) 45-50 degC, 2 h
7: 1.) n-butyllithium / 1.)THF, hexane, -78 degC to 0 degC 2.) room temperature, 12 h
With
N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; sodium acetate; pyridinium chlorochromate;
toluene-4-sulfonic acid;
In
tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/jo00183a018