Multi-step reaction with 9 steps
1: 1.) KOH / 1.) DMF, 2.) DMF, RT, overnight
2: SOCl2 / 1.) RT, 1 h, 2.) 80 deg C, 40 min
3: NaBH4, LiCl / tetrahydrofuran; ethanol / Ambient temperature
4: NaI, chlorotrimethylsilane / acetonitrile / 1.5 h
5: 1.) NaH / 1.) 1,2-dimethoxyethane, 0 deg C, 10 min, 2.) 1,2-dimethoxyethane, RT, 40 h
6: 1.) NaH / 1.) 1,2-dimethoxyethane, 0 deg C, 15 min, 2.) 1,2-dimethoxyethane, RT, 18 h
7: 70 percent / 20percent KOH / dimethylsulfoxide / 1.5 h / 60 - 70 °C
8: 51 percent / trifluoroacetic acid / 1 h / 90 °C
9: 47 percent / 4 N NaOH, O2 / ethanol / 24 h / Ambient temperature
With
potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; chloro-trimethyl-silane; thionyl chloride; oxygen; sodium hydride; trifluoroacetic acid; sodium iodide; lithium chloride;
In
tetrahydrofuran; ethanol; dimethyl sulfoxide; acetonitrile;
DOI:10.1021/jm00038a016