Multi-step reaction with 13 steps
1: 1.) triphenylphosphine / 1.) CH2Cl2, 0 deg C, 15 min, 2.) 15 min
2: 1.) n-butyllithium / 1.) THF, hexane, from -78 deg C to 25 deg C, 55 min, 2.) from -78 deg C to to 10 deg C, 100 min
3: K2CO3 / H2O; methanol / 4 h / 43 °C
4: tetrahydrofuran / 0.83 h / 25 °C
5: 86 mg / 4-(dimethylamino)pyridine (DMAP) / tetrahydrofuran / 16 h
6: 92 percent / acetone, p-toluenesulfonic acid / 3 h / 25 °C
7: 1.) potassium hexamethyldisilazide / 1.) THF, toluene, a) -78 deg C, 5 min, 0 deg C, 20 min, 2.) a) 0 deg C, 30 min, b) from 0 deg C to 25 deg C, 8 h
8: 71 percent Turnov. / acetic acid, tetrakis(triphenylphosphine)palladium(0), triphenylphosphine / tetrahydrofuran / 4 h / 25 °C
9: 94 percent / toluene / 2.5 h / Heating
10: 79 percent / 1.) H2, 2.) quinoline / 5percent Pd/BaSO4 / ethyl acetate / 25 °C / 1.) 4 min, 2.) 5 h
11: 85 percent / 48percent hydrofluoric acid / acetonitrile / 0.22 h / 25 °C
12: 36 percent Turnov. / CH3OC(O)NSO2NEt3 (Burgess reagent) / benzene / 25 - 50 °C
13: 66 percent / t-BuOK / 2-methyl-propan-2-ol / 0.17 h / 25 °C
With
quinoline; dmap; tetrakis(triphenylphosphine) palladium(0); n-butyllithium; Burgess Reagent; hydrogen fluoride; potassium tert-butylate; hydrogen; potassium hexamethylsilazane; potassium carbonate; toluene-4-sulfonic acid; acetic acid; triphenylphosphine; acetone;
Pd-BaSO4;
In
tetrahydrofuran; methanol; water; ethyl acetate; toluene; acetonitrile; tert-butyl alcohol; benzene;
DOI:10.1021/ja00181a035