Multi-step reaction with 7 steps
1: 1.) LDA / 1.) a) cyclohexane, -78 deg C, 30 min, b) cyclohexane, HMPA, -78 deg C, 15 min, 2.) cyclohexane, HMPA, 30 min
2: 89 percent / H2 / 4percent Pd/C / ethanol / 258.6 Torr
3: 85 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 4 h / Ambient temperature
4: DIBAL / diethyl ether; toluene / 0.75 h / -78 °C
5: diethyl ether; toluene; tetrahydrofuran / 0.5 h / -78 - 0 °C
6: 1.) NaH / 1.) ether, 0 deg C, 30 min, 2.) ether, 1 h
7: xylene / 2 h / Heating
With
hydrogen; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; toluene; xylene;
DOI:10.1021/jm00094a002