Multi-step reaction with 8 steps
1: 1.) Bu2SnO, 2.) nBu4NBr / 1.) toluene, reflux, 4 h, 2.) toluene, 20 deg C, 15 h
2: 94 percent / nBuN4F / tetrahydrofuran / 0.25 h / 20 °C
3: 99 percent / pyridine / 12 h / 0 °C
4: 78 percent / 3 Angstroem molecular sieves, N-iodosuccinimide / acetonitrile / 1.) 20 deg C, 10 min, 2.) 20 deg C, overnight
5: 1.) O3, 2.) PPh3 / 1.) CH2Cl2, -78 deg C, 2.) CH2Cl2
6: 63 percent / Bu3SnH, AIBN / benzene / 4 h / Heating
7: 73 percent / SmI2 / tetrahydrofuran / 0.17 h / 20 °C
8: 89 percent / acetonitrile / Heating
With
pyridine; N-iodo-succinimide; samarium diiodide; 2,2'-azobis(isobutyronitrile); 3 A molecular sieve; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; tri-n-butyl-tin hydride; di(n-butyl)tin oxide; ozone; triphenylphosphine;
In
tetrahydrofuran; acetonitrile; benzene;
DOI:10.1002/(SICI)1521-3765(19990201)5:2<430::AID-CHEM430>3.0.CO;2-D