sodium methylate in N,N-dimethyl-formamide T=0 - 100°C; Wittig-Horner olefination; 4 h; Inert atmosphere;

lithium diisopropyl amide in tetrahydrofuran; hexane a.) -50 deg C, 30 min, b.) RT, 1.5 h;

benzyl-N,N-dimethylamine; palladium diacetate in xylene T=120°C; 4.5 h;

pyridine; titanium tetrachloride; zinc in 1,4-dioxane 0.133333 h; microwave irradiation;

2,2'-azo-bisisobutyronitrile in tetrahydrofuran 8 h; Reflux;

in cyclohexane; acetone; toluene

lithium methanolate in methanol; N,N-dimethyl-formamide T=90°C; 1 h; Title compound not separated from byproducts;

1: 3,4,5-Trimethoxybenzyltriphenylphosphonium Bromide With n-butyllithium in tetrahydrofuran; hexane T=0°C; Wittig type reaction; 2: 3,4,5-trimethoxy-benzyl alcohol With 4,4'-di-tert-butylbiphenyl; lithium; nickel dichloride in tetrahydrofuran; hexane Wittig type reaction; 24 h; Inert atmosphereReflux; 3: With 2,2'-azo-bisisobutyronitrile; diphenyldisulfane in tetrahydrofuran 8 h; Reflux;

1: 3,4,5-Trimethoxybenzyltriphenylphosphonium Bromide With n-butyllithium in tetrahydrofuran; hexane T=0°C; Wittig type reaction; 2: 3,4,5-trimethoxy-benzyl alcohol With 4,4'-di-tert-butylbiphenyl; lithium; nickel dichloride in tetrahydrofuran; hexane Wittig type reaction; 24 h; Inert atmosphereReflux; optical yield given as percent de;

1: PBr3 / CH2Cl2 / 0.75 h / -5 °C 2: 73 percent / 2.17 h / 140 - 180 °C 3: 61 percent / NaH; 15-crown-5 / tetrahydrofuran View Scheme