Multi-step reaction with 10 steps
1.1: 95 percent / ethanol; CH2Cl2 / 0 °C
2.1: 94 percent / 2-methoxy-ethanol / 2 h / Heating
3.1: 98 percent / MgBr2; pyridine / 1.5 h / Heating
4.1: NaH / dimethylformamide / 1 h / 20 °C
4.2: 83 percent / dimethylformamide / 1 h / 0 °C
5.1: 88 percent / PPh3; DTAD / CH2Cl2 / 1 h / 20 °C
6.1: 100 percent / K2CO3; PhSH / 1-methyl-pyrrolidin-2-one / 0.58 h / 195 °C
7.1: 57 percent / pyridine / 2 h / 120 °C
8.1: 66 percent / PPh3; CCl4 / 1,2-dichloro-ethane / 2 h / 70 °C
9.1: 84 percent / propan-2-ol / 0.5 h / 80 °C
10.1: 97 percent / ammonia / methanol / 20 °C
With
pyridine; tetrachloromethane; ammonia; sodium hydride; potassium carbonate; thiophenol; triphenylphosphine; magnesium bromide;
In
1-methyl-pyrrolidin-2-one; methanol; ethanol; dichloromethane; 2-methoxy-ethanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide; isopropyl alcohol;
5.1: Mitsunobu reaction;
DOI:10.1021/jm060434q