Multi-step reaction with 6 steps
1: 1.) NaH, 3.) pyridinium dichromate
2: 90 percent / oxalyl chloride, DMF / CH2Cl2 / 0 - 20 °C
3: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 25 min, 2.) THF, hexane, from -78 deg C to RT
4: 1.) diisopropylamine, n-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, from -78 deg C to RT
5: 85 percent / 1,4-cyclohexadiene / 20percent Pd(OH)2/C / ethanol / 65 °C
6: 75 percent / Ph3P, DEAD / tetrahydrofuran / 18 h / Ambient temperature
With
dipyridinium dichromate; n-butyllithium; oxalyl dichloride; cyclohexa-1,4-diene; sodium hydride; diisopropylamine; N,N-dimethyl-formamide; triphenylphosphine; diethylazodicarboxylate;
palladium dihydroxide;
In
tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1021/jm00014a010