1: 4-methoxy pyridine With lithium diisopropyl amide in tetrahydrofuran; n-heptane; ethylbenzene T=-25°C; 0.5 h; 2: triisopropylsilyl chloride in tetrahydrofuran; n-heptane; ethylbenzene T=-25 - 20°C; 16.25 h;

2: 1) NaOMe, 2) oxalic acid / 1) MeOH 3: 94 percent / 1) n-BuLi 4: 92 percent / POCl3, DMF / trichloroethene / Ambient temperature 5: 1) H2, Li2CO3, 2) H2 / 1) Pt/C, 2) Pd/C / EtOH View Scheme

2: 1) NaOMe, 2) oxalic acid / 1) MeOH 3: 94 percent / 1) n-BuLi 4: 92 percent / POCl3, DMF / trichloroethene / Ambient temperature 5: 1) H2, Li2CO3, 2) H2 / 1) Pt/C, 2) Pd/C / EtOH View Scheme

1: toluene / 0.75 h / -23 °C 2: 88 percent / diethyl ether / 1.5 h / -78 °C 3: 86 percent / NaOMe, oxalic acid / methanol / 1.) reflux, 12 h, 2.) room temp., 5 h 4: 94 percent / n-BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C 5: 96 percent / POCl3, DMF / trichloroethene / Ambient temperature 6: 89 percent / H2, Li2CO3 / 5percent Pt/C, 5percent Pd/C / ethanol / 9 h / Ambient temperature; 1.) 6 h, 2.) 3 h View Scheme