Multi-step reaction with 10 steps
1: 40 percent / 132 h / 110 °C
2: 81 percent / 10percent aq. NaOH / tetrahydrofuran / 5 h / 25 °C
3: 90 percent / p-toluenesulfonic acid / ethanol / 24 h / 70 °C
4: 99 percent / zinc / ethanol / 1 h / Heating
5: 60 percent / sodium iodide, diisopropylethylamine / dimethylsulfoxide / 120 h / 25 °C
6: 1.) n-butyllithium / 1.) THF, hexane, a) -78 deg C, 30 min, b) 0 deg C, 4 h, 2.) 25 deg C, 24 h
7: 2.) 25percent aq. acetic acid / 1.) acetonitrile, reflux, 6.5 d, 2.) tetrahydrofuran, 24 deg C, 3 h
8: 64 percent / triethylaluminum / hexane; benzene / 7 h / 25 °C
9: 1.) BH3-THF, 2.) 3 N NaOH, 30percent H2O2 / 1.) THF, 25 deg C, 20 h, 2.) -10 deg C, 20 min
10: 1.) n-butyllithium / 1.) tetrahydrofuran, hexane, -78 deg C, 1 h, 2.)a) -78 deg C, 1 h, b) -40 deg C, 3 h
With
sodium hydroxide; n-butyllithium; borane-THF; dihydrogen peroxide; triethylaluminum; toluene-4-sulfonic acid; acetic acid; N-ethyl-N,N-diisopropylamine; sodium iodide; zinc;
In
tetrahydrofuran; ethanol; hexane; dimethyl sulfoxide; benzene;