Multi-step reaction with 13 steps
1: 89.2 percent / molecular sieves (4A) / boron trifluoride etherate (BF3*Et2O) / CH2Cl2 / 1.) 20 deg C, 2 h; 2.) 0-5 deg C, 48 h
2: 82 percent / NaOMe / methanol / 1.) 20 deg C, 10 min; 2.) 0-4 deg C, 12 h
3: 1.) Et3N; 2.) aq. trifluoroacetic acid (50percent) / 1.) TsOH*H2O / 1.) 20 deg C, 12 h; 2.) CH2Cl2, 20 deg C, 15 min
4: 90.6 percent / NaH / dimethylformamide / 12 h / 20 °C
5: 84.6 percent / aq. HBF4 (50percent), NaHCO3 / methanol / 3 h / 20 °C
6: 1.) Bu2SnO; 2.) Bu4NBr / 1.) benzene, reflux, 8 h; 2.) 45 deg C, 5 h
7: 72 percent / NaH / dimethylformamide / 12 h / 20 °C
8: 78.8 percent / t-BuOK / dimethylsulfoxide / 0.33 h / 80 °C
9: 95 percent / pyridine / 12 h / 20 °C
10: bromine / CH2Cl2 / 0.33 h / 0 °C
11: 34.8 percent / molecular sieves (4A) / Et4NBr / dimethylformamide; CH2Cl2 / 72 h / 20 °C
12: 96.1 percent / NaOMe / methanol / 12 h / 20 °C
13: 1.) Hg(CN)2, molecular sieves (4A); 2.) NaOMe / 1.) CH3NO2, CH2Cl2, 20 deg C, 36 h; 2.) MeOH, 20 deg C, 12 h
With
pyridine; tetrafluoroboric acid; 4 A molecular sieve; potassium tert-butylate; tetrabutylammomium bromide; bromine; sodium methylate; mercury(II) cyanide; sodium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; triethylamine; trifluoroacetic acid;
boron trifluoride diethyl etherate; tetraethylammonium bromide; toluene-4-sulfonic acid;
In
methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/0008-6215(88)84110-7