Multi-step reaction with 16 steps
1: 95 percent / thionyl chloride, pyridine / CH2Cl2 / 3 h / Ambient temperature
2: 88 percent / dimethylformamide / 7 h / Ambient temperature
3: 91 percent / 30percent aq. sodium hydroxide / methanol / 72 h / Heating
4: 95 percent / potassium carbonate / acetone / 3 h / Heating
5: 95 percent / lithium aluminium hydride / diethyl ether / 2 h / Heating
6: 85 percent / pyridine / CHCl3 / 3 h / 0 °C
7: 94 percent / 1,2-dimethoxyethane / dimethylsulfoxide / 18 h / Ambient temperature
8: 81 percent / ether / benzene / 1 h / Ambient temperature; aq. hydrochloric acid, ethyl acetate, 16 h
9: 98 percent / trifluoroacetic anhydride, / nitromethane / 1.5 h / 0 °C
10: 81 percent / H2, conc. hydrochloric acid (4 drops) / 10percent palladized charcoal / ethyl acetate
11: 73 percent / potassium cyanoferrate(III), potassium carbonate / H2O; dioxane / 0.17 h
12: 70 percent / various solvent(s) / 0.17 h / Heating
13: 94 percent / potassium carbonate / dimethylformamide / Ambient temperature
14: 66 percent / sodium methoxide / methanol / 3 h / Ambient temperature
15: 82 percent / potassium carbonate / dimethylformamide / 5 h / Ambient temperature
16: 1.) boron trichloride, 2.) H2 / 10percent palladized chacoal / 1.) dichloromethane, -10 deg C, 0.5 h, 2.) ethyl acetate, conc. hydrochloric acid (1 drop)
With
pyridine; hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; 1,2-dimethoxyethane; thionyl chloride; diethyl ether; hydrogen; sodium methylate; boron trichloride; potassium carbonate; trifluoroacetic anhydride; potassium hexacyanoferrate(III);
palladium on activated charcoal;
In
1,4-dioxane; methanol; diethyl ether; nitromethane; dichloromethane; chloroform; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetone; benzene;