Multi-step reaction with 10 steps
1.1: 98 percent / [(benzylidene)(PCy3)(1,3-dimesitylimidazolidin-2-yl)RuCl2] / CH2Cl2 / 36 h / 20 °C
2.1: 778.8 mg / hydrogen / Pd/C / ethyl acetate / 18 h / 20 °C
3.1: 29 mg / K2CO3; methanol / 18 h / 20 °C
4.1: 100 percent / i-Pr2NEt / CH2Cl2 / 24 h / 20 °C
5.1: 95 percent Turnov. / sodium methoxide / methanol / 12 h / Heating
6.1: 88 percent / triphenylphosphine; imidazole; iodine / benzene / 2 h / Heating
7.1: 90 percent / N,N-diisopropylethylamine / toluene; acetonitrile / 24 h / Heating
8.1: BuLi / hexane; tetrahydrofuran / 0.5 h / 0 °C
8.2: 44 percent / hexane; tetrahydrofuran / -78 - 20 °C
9.1: 89 percent / hydrogen / chlorotris(triphenylphosphine)rhodium(I) / benzene; ethanol / 12 h
10.1: 71 percent / AcCl; MeOH / CH2Cl2 / 2 h / 20 °C
With
1H-imidazole; methanol; n-butyllithium; hydrogen; iodine; sodium methylate; potassium carbonate; N-ethyl-N,N-diisopropylamine; acetyl chloride; triphenylphosphine;
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; palladium on activated charcoal; Wilkinson's catalyst;
In
tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; ethyl acetate; toluene; acetonitrile; benzene;
8.2: Wittig reaction;
DOI:10.1021/jo049955g