Multi-step reaction with 8 steps
1: SOCl2 / benzene / 3 h / Heating
2: 0.33 h / Heating
3: 68 percent / ethanol / 6 h / 100 °C
4: 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
5: 95 percent / LiAlH4 / tetrahydrofuran / 2 h / 0 °C
6: 96 percent / MnO2 / 20 h / Ambient temperature
7: 93 percent / tetrahydrofuran / 0.25 h
8: 62 percent / 1,1,1-tris(acetoxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-one / CH2Cl2 / 0.5 h / Ambient temperature
With
1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; manganese(IV) oxide; lithium aluminium tetrahydride; thionyl chloride; Dess-Martin periodane; lithium hexamethyldisilazane;
In
tetrahydrofuran; ethanol; dichloromethane; benzene;
DOI:10.1021/jm00070a012