sodium methylate in toluene T=100°C; 4 h;

1: thiophene-2-carboxylic acid With 1,1'-carbonyldiimidazole in tetrahydrofuran T=20°C; 10 h; 2: magnesium salt of monomethyl malonic acid in tetrahydrofuran T=20°C; 18 h; Further stages.;

triethylamine; magnesium chloride in acetonitrile T=20°C; 12 h;

4-(N,N-dimethlyamino)pyridine; MgBr2(Et2O); N-ethyl-N,N-diisopropylamine in dichloromethane 48 h; Inert atmosphereReflux;

hydrogenchloride; 1,1'-carbonyldiimidazole in tetrahydrofuran; methanol

lithium diisopropyl amide in tetrahydrofuran T=-78°C; 2 h;

1: SOCl2 / 0.75 h / 50 °C 2: 86 percent / MgCl2; Et3N / acetonitrile / 12 h / 20 °C View Scheme

1.1: H2 / RuBr2((R)-(6,6'-(MeO)2-biphenyl-2,2'-diyl)bis(Ph2-phosphane) / methanol / 72 h / 25 °C / 760.05 Torr 2.1: 82 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 1.5 h / 0 - 20 °C 3.1: 78 percent / Et3N / diethyl ether / 3 h / -10 - 0 °C 4.1: 94 percent / tetrahydrofuran; H2O / 3 h / 65 °C 5.1: NaH / N,N-dimethyl-acetamide / 1.5 h / 50 °C 5.2: 62 percent / N,N-dimethyl-acetamide / 2.5 h / 80 °C View Scheme

1.1: H2 / RuBr2((R)-(6,6'-(MeO)2-biphenyl-2,2'-diyl)bis(Ph2-phosphane) / methanol / 72 h / 25 °C / 760.05 Torr 2.1: 82 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 1.5 h / 0 - 20 °C 3.1: 78 percent / Et3N / diethyl ether / 3 h / -10 - 0 °C 4.1: 94 percent / tetrahydrofuran; H2O / 3 h / 65 °C 5.1: NaH / N,N-dimethyl-acetamide / 1.5 h / 50 °C 5.2: 62 percent / N,N-dimethyl-acetamide / 2.5 h / 80 °C View Scheme

1: H2 / RuBr2((R)-(6,6'-(MeO)2-biphenyl-2,2'-diyl)bis(Ph2-phosphane) / methanol / 72 h / 25 °C / 760.05 Torr 2: 82 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 1.5 h / 0 - 20 °C 3: 78 percent / Et3N / diethyl ether / 3 h / -10 - 0 °C 4: 94 percent / tetrahydrofuran; H2O / 3 h / 65 °C View Scheme