1: (E)-1-hex-3-enyl bromide With magnesium in tetrahydrofuran Metallation; 6 h; 2: With manganese (II) chloride in tetrahydrofuran Transmetallation; 12 h; 3: 1-acetoxy-6-bromohexane With lithium chloride; copper dichloride in tetrahydrofuran; 1-methyl-pyrrolidin-2-one T=0 - 5°C; Coupling reaction;

pyridine T=20°C; Acetylation; 12 h;

indium trifluoromethanesulfonate T=80°C; retro-Claisen condensation; 24 h;

4-(bromomethylene)morpholin-4-ium bromide in dichloromethane T=0°C; 2.5 h; Inert atmosphere;

acetic acid T=125 - 130°C;

1: 65 percent / aq. HBr / 2 h / Heating 2: 98 percent / pyridine / 12 h / 20 °C View Scheme

1: benzene / 2 h / Heating 2: NaOH / H2O / 24 h / Heating View Scheme