Multi-step reaction with 7 steps
1: 92 percent / Ph3P, CBr4 / diethyl ether / 2.5 h / Ambient temperature
2: 90 percent / NaI / acetone / 3 h / Heating
3: 96 percent / 20 h / 70 °C
4: 1.) KN(TMS)2, HMPA / 1.) THF, room temp., 20 min; -78 deg C, 10 min, 2.) -78 deg C to room temp., 1 h; room temp., 1 h
5: 91 percent / n-Bu4NF / tetrahydrofuran / 8 h / Ambient temperature
6: 67 percent / AIBN, thiophenol / benzene / 5 h / Heating
7: Ag2O / CD2Cl2 / 0.42 h / Ambient temperature
With
N,N,N,N,N,N-hexamethylphosphoric triamide; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; thiophenol; triphenylphosphine; sodium iodide; silver(l) oxide;
In
tetrahydrofuran; diethyl ether; dichloromethane-d2; acetone; benzene;
DOI:10.1021/jo00071a024