Multi-step reaction with 7 steps
1: 57 percent / p-toluenesulfonic acid / ethane-1,2-diol; CHCl3; acetonitrile / 0.33 h / Ambient temperature
2: NaH / dimethylformamide / Ambient temperature
3: BF3*Et2O / CH2Cl2 / 0.08 h / Ambient temperature
4: 1.) 3A molecular sieves, trimethylsilyl trifluoromethanesulfonate, 2.) 42percent aq. tetrafluoroboric acid / 1.) Et2O, CH2Cl2, -55 deg C, 0.5 h, 2.) MeCN, RT, 0.5 h
5: 1.) dibutyltin oxide, 2.) KI, CsF / 1.) MeOH, reflux, 2 h, 2.) DMF, RT, overnight
6: NaH / dimethylformamide / 1 h / Ambient temperature
7: CF3COOH / CH2Cl2 / 1 h / Ambient temperature
With
tetrafluoroboric acid; trimethylsilyl trifluoromethanesulfonate; 3 A molecular sieve; boron trifluoride diethyl etherate; sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; cesium fluoride; trifluoroacetic acid; potassium iodide;
In
dichloromethane; chloroform; ethylene glycol; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/0008-6215(95)00012-I