Multi-step reaction with 7 steps
1: 0.33 h / Heating
2: 68 percent / ethanol / 6 h / 100 °C
3: 1.) 1,3-dimethyl-3,4,5,6-tetrahydro-2-pyrimidinone, LiN(TMS)2 / 1.) THF, 0 deg C, 10 min, 2.) THF, RT, 90 min
4: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 0 °C
5: 96 percent / MnO2 / 20 h / Ambient temperature
6: 1.) LDA / 1.) hexane, THF, 0 deg C, 20 min, 2.) hexane, THF, -78 deg C, 45 min
7: 88percent aq. HCOOH / CH2Cl2 / 2 h / Ambient temperature
With
1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; manganese(IV) oxide; lithium aluminium tetrahydride; formic acid; lithium hexamethyldisilazane; lithium diisopropyl amide;
In
tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1021/jm00070a012