Multi-step reaction with 12 steps
1: 99 percent / LiBH4 / tetrahydrofuran / 1.5 h / Ambient temperature
2: 93 percent / pyridine / 1.5 h / Ambient temperature
3: 1.) POCl3, 2.) NaBH4 / 1.) toluene, reflux, 1.5 h, 2.) MeOH, -78 deg C, 1 h
4: 86 percent / aq. K2CO3 / methanol / 1 h / Ambient temperature
5: 91 percent / NaOEt / ethanol / 6 h / Heating
6: 90 percent / anisole, mercuric trifluoroacetate / ethanol / 14.5 h / Ambient temperature
7: 1.) NaH / 1.) DMF, RT, 2.) DMF, 100 deg C, 3 h
8: 82 percent / NaBH4 / methanol / 1 h / Ambient temperature
9: SOCl2 / 1 h / Ambient temperature
10: 1.) BuLi, diisopropylamine / 1.) THF, hexane, -78 deg C, 40 min, 2.) THF, hexane, a) -78 deg C, 2 h, b) -50 deg C, 20 h
11: 71 percent / 0.25N aq. HCl / methanol / 8.5 h / Ambient temperature
12: 83 percent / aq. MeOH / Raney Ni / 1 h / Heating
With
pyridine; hydrogenchloride; methanol; sodium tetrahydroborate; lithium borohydride; n-butyllithium; thionyl chloride; sodium ethanolate; mercury(II) trifluoroacetate; sodium hydride; potassium carbonate; methoxybenzene; diisopropylamine; trichlorophosphate;
nickel;
In
tetrahydrofuran; methanol; ethanol;
DOI:10.1248/cpb.47.83