Multi-step reaction with 13 steps
1.1: 58 percent / Cl2[(c-C6H11)3P](1,3-dimesitylimidazolidin-2-ylidene)Ru=CHPh / toluene / 20 - 70 °C
2.1: CH2Cl2; acetone / 1 h / 0 °C
3.1: BF3*OEt2; triethylsilane / acetonitrile / -40 - 20 °C
4.1: 77 percent / triethylamine; 4-(dimethylamino)pyridine / CH2Cl2
5.1: sodium hydride; tetrabutylammonium iodide / tetrahydrofuran / 6 h / Heating
6.1: 410 mg / diethyl ether; H2O / 1 h / 20 °C
7.1: 70 percent / Cl2[(c-C6H11)3P](1,3-dimesitylimidazolidin-2-ylidene)Ru=CHPh / CH2Cl2 / Heating
8.1: Mg2SO4; acetic acid / benzene / 0.83 h / 20 °C
9.1: t-BuLi / tetrahydrofuran; pentane / 0.08 h / -78 °C
9.2: tetrahydrofuran; pentane / 0.33 h / -78 - 20 °C
10.1: 89.4 mg / CuCl2 / tetrahydrofuran; H2O / 1 h / 20 °C
11.1: cerium(III) chloride heptahydrate; sodium borohydride / methanol / 1 h / -78 °C
12.1: sodium hydride / tetrahydrofuran / 6 h / Heating
13.1: 19.6 mg / diethyl ether; H2O / 1.5 h
With
triethylsilane; dmap; sodium tetrahydroborate; cerium(III) chloride; boron trifluoride diethyl etherate; tert.-butyl lithium; tetra-(n-butyl)ammonium iodide; sodium hydride; magnesium sulfate; acetic acid; triethylamine; copper dichloride;
Cl2[(c-C6H11)3P](1,3-dimesitylimidazolidin-2-ylidene)Ru=CHPh;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone; toluene; acetonitrile; pentane; benzene;
DOI:10.1021/ol0706096