Multi-step reaction with 9 steps
1: 90 percent / K2CO3 / acetone / 48 h / Heating
2: 62 percent / pyridinium chlorochromate / acetone / 2.5 h / Ambient temperature
3: 100 percent / pyridine / Ambient temperature
4: 1.) NaH / 1.) benzene, reflux, 2 h, 2.) benzene, reflux, overnight
5: 56 percent / pyridine / Ambient temperature
6: 100 percent / CoCl2, NaBH4 / tetrahydrofuran; ethanol / 1.) 0 deg C, 10 min, 2.) RT, overnight
7: 96 percent / aq. NaOH / methanol / Ambient temperature
8: 85 percent / PBr3 / tetrahydrofuran / 1.) 0 deg C, 10 min, 2.) RT, overnight
9: 83 percent / Ce(NH4)2(NO3)6 / acetonitrile; H2O
With
pyridine; sodium hydroxide; sodium tetrahydroborate; ammonium cerium(IV) nitrate; phosphorus tribromide; sodium hydride; potassium carbonate; pyridinium chlorochromate;
In
tetrahydrofuran; methanol; ethanol; water; acetone; acetonitrile;
DOI:10.1021/jm00366a004