Multi-step reaction with 6 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
With
potassium hydroxide; sodium tetrahydroborate; chloro-trimethyl-silane; thionyl chloride; sodium hydride; sodium iodide; lithium chloride;
In
tetrahydrofuran; ethanol; acetonitrile;
DOI:10.1021/jm00038a016