Multi-step reaction with 9 steps
1: 93.2 percent / K2CO3 / acetone / 18 h / Heating
2: 62 percent / NaN3, NH4Cl / dimethylformamide / 24 h / 110 °C
3: 67 percent / K2CO3 / acetonitrile / 1 h / Heating
4: 96 percent / BBr3 / CH2Cl2
5: 84 percent / Ph3P, DEAD / CH2Cl2 / 12 h
6: 37.5 percent / triethylamine / CHCl3 / 18 h / Heating
7: 72.3 percent / LiOH, H2O / ethanol / a) RT, 12 h, b) reflux, 2 h
8: 1.) 1,1'-carbonyldiimidazole / 1.) CHCl3, 2.) CHCl3, 12 h
9: 93.5 percent / tetrahydrofuran; diethyl ether / 1 h
With
lithium hydroxide; sodium azide; water; boron tribromide; potassium carbonate; ammonium chloride; triethylamine; triphenylphosphine; 1,1'-carbonyldiimidazole; diethylazodicarboxylate;
In
tetrahydrofuran; diethyl ether; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1021/jm00074a004