Multi-step reaction with 17 steps
1: 1.) NaH / 1.) DMF, 0 deg C, 5 min, 2.) RT, 1 h
2: 80percent aq. acetic acid / 4 h / 100 °C
3: concd. H2SO4 / 4 h / Ambient temperature
4: 82 percent / sodium methoxide / methanol / 0.08 h / Ambient temperature
5: 64 percent / pyridine, triethylamine / 6 h / Ambient temperature
6: 60 percent / benzene / 3 h / Heating
7: 88 percent / camphorsulfonic acid / acetone / 2 h / Ambient temperature
8: H2 / Raney nickel W-4 / ethanol / 36 h / 760 Torr / Ambient temperature
9: Bu4NF / tetrahydrofuran / 4 h / Ambient temperature
10: pyridine / 3 h / 40 °C
11: K2CO3 / dioxane; H2O / 2 h / 90 °C
12: 64 percent / cyclohexene, 20percent Pd(OH)2/C / ethanol / 26 h / Heating
13: 83 percent / pyridine / 4 h / Ambient temperature
14: 84 percent / dimethylformamide / 0.5 h / 140 °C
15: BH3-Me2S / tetrahydrofuran / 2 h / Ambient temperature
16: K2CO3 / methanol / 2 h / 65 °C
17: 84 percent / 1 M aq. HCl / 0.5 h / Heating
With
pyridine; hydrogenchloride; palladium dihydroxide; dimethylsulfide borane complex; sulfuric acid; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; sodium hydride; potassium carbonate; acetic acid; triethylamine; cyclohexene;
Raney nickel W-4;
In
tetrahydrofuran; 1,4-dioxane; methanol; ethanol; water; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1021/jo00257a003