Multi-step reaction with 9 steps
1: 78 percent / diethyl ether / 1 h / Ambient temperature
2: 61 percent / pyridinium p-toluenesulfonate / ethanol / 4 h / 60 - 70 °C
3: 88 percent / pyridinium chlorochromate (PCC), NaOAc / CH2Cl2 / 8 h / Ambient temperature
4: 84 percent / dimethylformamide / 80 °C
5: 1) lithium diisopropylamide / 1) THF, -60 deg C, 20 min, 2) -60 to -5 deg C
6: 1) lithium diisopropylamide / 1) THF, -70 deg C, 15 min, 2) -70 deg C, 1 h
7: 30 percent aq. acetic acid / tetrahydrofuran / 3 h / Ambient temperature
8: 71 percent / triethylamine, 4-dimethylaminopyridine / 48 h / Ambient temperature
9: 40 percent / triethylamine, 4-dimethylaminopyridine / 7 h / ice-NaCl bath
With
dmap; sodium acetate; pyridinium p-toluenesulfonate; acetic acid; triethylamine; pyridinium chlorochromate; lithium diisopropyl amide;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1271/bbb1961.54.1531