Multi-step reaction with 8 steps
1: 64 percent / acetic acid / 3 h / 60 °C
2: 50 percent / phosphorus oxychloride / 48 h / 70 °C
3: 1.) sodium hydride / 1.) THF, 0 deg C, 10 min, 2.) THF, -78 deg C - RT, 1 h
4: 66 percent / Raney nickel / formic acid / 60 °C
5: 1.) lithium diisopropylamide, 2.) MgBr2
6: 81 percent / methanol / 16 h
7: 1.) lithium diisopropylamide / 1.) hexane, THF, -45 deg C, 1 h, 2.) hexane, THF, -45 deg C - -20 deg C, 3.5 h
8: 1.) triethylborane, pivalic acid, 2.) sodium borohydride / 1.) THF, methanol, 30 min, 2.) THF, methanol, -78 deg C, 6 h
With
sodium tetrahydroborate; triethyl borane; sodium hydride; magnesium bromide; lithium diisopropyl amide; trichlorophosphate; Trimethylacetic acid;
nickel;
In
methanol; formic acid; acetic acid;
DOI:10.1021/jm00089a022