1H-imidazole in N,N-dimethyl-formamide T=20°C; silylation;

in tetrahydrofuran

4-(bromomethylene)morpholin-4-ium bromide in dichloromethane T=0°C; 2 h; Inert atmosphere;

1: BH3*OEt2 / tetrahydrofuran 2: Et3N, DMAP View Scheme

1: 46 percent / 48percent HBr / 72 h / 90 °C 2: 88 percent / Et3N, DMAP / CH2Cl2 / 24 h / Ambient temperature View Scheme

1H-imidazole in N,N-dimethyl-formamide Substitution; Title compound not separated from byproducts;

dimethylsulfide; triethylamine 1.) CH2Cl2, -50 deg C, 30 min 2.) -50 deg C, 1h; Yield given. Multistep reaction;

2,6-dimethylpyridine 1.) dichloromethane, room t., 2 h; 2.) 0 degC, 2 h; Yield given. Multistep reaction;

sodium iodide in acetone Heating;

1.1: BuLi / tetrahydrofuran / 3 h / 20 °C 1.2: 85 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / 0 °C 2.1: 75 percent / Al2O3; H2O / 20 h / 20 °C 3.1: 46 percent / pyridine / 16 h / 0 °C 4.1: 66 percent / Li2CuCl4 / tetrahydrofuran / 12 h / 20 °C 5.1: 98 percent / LDA / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - -50 °C 6.1: 92 percent / p-TsOH / methanol / 16 h / 20 °C 7.1: 88 percent / Na(Hg); Na2HPO4 / methanol / 21 h / 20 °C 8.1: 91 percent / LiAlH4 / tetrahydrofuran / Heating View Scheme