Multi-step reaction with 8 steps
1: 5.02 g / dimethylformamide / 2 h / Ambient temperature
2: pyridinium toluene-p-sulfonate / methanol / 1.5 h / 55 °C
3: 2.) K2CO3 / 1.) CH2Cl2, 0 deg C, 30 min, 2.) CH3OH, H2O, 0 deg C, 100 min
4: PPh3, CBr4, Et3N / CH2Cl2 / 1 h / -20 °C
5: CH2Cl2; hexane / 1 h / -20 °C
6: 1.) Na2CO3, Et3OBF4, 2.) acetic acid, H2O / 1.) CH2Cl2, room temperature, 90 min, 2.) THF, room temperature, overnight
7: 84 percent / Et3N / CH2Cl2 / 2.75 h / Ambient temperature
8: 87 percent / Bu4NF / tetrahydrofuran / 0.83 h / Ambient temperature
With
carbon tetrabromide; tetrabutyl ammonium fluoride; water; triethyloxonium fluoroborate; pyridinium p-toluenesulfonate; sodium carbonate; potassium carbonate; acetic acid; triethylamine; triphenylphosphine;
In
tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;