Multi-step reaction with 10 steps
1: 2.) 1 M aq. HCl / 1.) pyridinium p-toluenesulfonate / 1.) 50 deg C, 1 h, 2.) THF, 24 - 25 deg C, 1 h
2: 95 percent / Dess-Martin reagent / CH2Cl2 / 0.5 h / Ambient temperature
3: 43 percent / DABCO / dimethylformamide / 1 h
5: 99 percent / CeCl3*7H2O, NaBH4 / ethanol / 0.5 h / Ambient temperature
6: 69 percent / NaH / dimethylformamide; paraffin / 3 h / Ambient temperature
7: 93 percent / n-Bu4NF / tetrahydrofuran / 3 h / Ambient temperature
8: 100 percent / NaH / dimethylformamide; paraffin / 2 h / Ambient temperature
9: 55 percent / 85percent MCPBA / CHCl3 / 24 h / Ambient temperature
10: 99 percent / DDQ, H2O / CH2Cl2 / 3 h / 24 °C
With
1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; sodium tetrahydroborate; cerium(III) chloride; tetrabutyl ammonium fluoride; water; sodium hydride; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
pyridinium p-toluenesulfonate;
In
tetrahydrofuran; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; paraffin;
DOI:10.1021/jo00095a021