Multi-step reaction with 15 steps
1: 1.) p-TsOH, 2.) LiAlH4 / 1.) CH2Cl2, 0 deg C, 4 h, 2.) THF, 60 deg C, 4 h
2: pyridine / CH2Cl2 / 24 h / Ambient temperature
3: 48 percent / 18-crown-6 / dimethylformamide / 3 h / 60 - 80 °C
4: 63 percent / KOH / H2O; ethanol / 48 h / 140 °C
5: 79 percent / CH2Cl2
6: 1.) n-BuLi, dicyclohexylamine, 2.) I2 / tetrahydrofuran / 1.) -78 deg C, 10 min -> room temperature, 5 min, 2.) -78 deg C, 5 min
7: 1.) silver trifluoroacetate, silver oxide, 2.) KOH / 1.) CH3CN, Et2O, room temperature, 20 h, 2.) THF, CH3OH, room temperature, 16 h
8: CH2Cl2 / 0 °C
9: 68 percent / pyridine / CH2Cl2 / 4 h / Ambient temperature
10: 293 mg / 18-crown-6, KF / dimethylformamide / 15 h / 70 °C
11: 73 percent
12: 2.) pyridine / 1.) Et2O, room temperature, 20 min, 2.) CH2Cl2, room temperature, 12 h
13: 18 percent / 1.) NBS, 2.) s-collidine / 1.) CCl4, reflux, 45 min, 2.) xylene, reflux, 10 min
14: 2.5 mg / KOH / tetrahydrofuran; methanol / 16 h / Ambient temperature
15: 0.52 mg / benzene; ethanol / irradiation, 2.5 min -> reflux, 1 h
With
pyridine; 2,4,6-trimethyl-pyridine; potassium fluoride; potassium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; 18-crown-6 ether; iodine; silver trifluoroacetate; toluene-4-sulfonic acid; N-cyclohexyl-cyclohexanamine; silver(l) oxide;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;