Multi-step reaction with 9 steps
1: NaH (60percent, dispersion im oil) / dimethylformamide / 20 h / Ambient temperature
2: 86 percent / aq. 80percent acetic acid / CH2Cl2 / 2 h / 80 °C
3: 71.6 percent / pyridine / CH2Cl2 / 1) -78 deg C, 3 h: 2) 0 deg C, 1 h
4: 52 percent / 4-dimethylaminopyridine / acetonitrile / 5 h / Heating
5: 91 percent / 2,2'-azobis(isobutyronitrile), tribuylstannane / toluene / 2 h / 80 °C
6: 95 percent / sodium methoxide / methanol / 5 h / Ambient temperature
7: 76 percent / silver trifluoromethanesulfonate, tetramethylurea / CH2Cl2 / 2 h
8: 82 percent / sodium methoxide / methanol
9: 74 percent / silver trifluoromethanesulfonate, sym-collidine, molecular sieve (4 Angstroem) / CH2Cl2 / 1 h / Ambient temperature
With
pyridine; 2,4,6-trimethyl-pyridine; dmap; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; tri-n-butyl-tin hydride; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; acetic acid; tetramethylurea;
In
methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/0008-6215(88)84115-6