water; iodine; sodium hydrogencarbonate in acetone

triethylamine; 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide in various solvent(s) T=80°C; Stetter reaction; 10 h;

2-hydroxy-1,3-isoindolinedione; dibenzoyl peroxide in toluene T=80°C;

1: n-butyllithium; Mo(CO)6 in diethyl ether; hexane T=-60°C; Addition; 2: With boron trifluoride diethyl etherate in diethyl ether; hexane T=-60°C; Substitution; 0.25 h; 3: acrylonitrile in diethyl ether; hexane T=-60 - 20°C; Addition; Further stages.;

3-(2-Ethoxyethyl)-5-(2-hydroxyethyl)-4-methyl-1,3-thiazoliumbromid; triethylamine in 1,4-dioxane T=80°C; 12 h;

in tetrahydrofuran

1.1: N-bromosuccinmide / 0.33 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / -40 - -10 °C / |Inert atmosphere 2.2: -78 - -20 °C / |Inert atmosphere 3.1: 18-crown-6 ether / dimethyl sulfoxide / 4 h / 100 °C / |Inert atmosphere 4.1: iodine; sodium hydrogencarbonate; water / acetone View Scheme

1.1: n-butyllithium / tetrahydrofuran; hexane / -40 - -10 °C / |Inert atmosphere 1.2: -78 - -20 °C / |Inert atmosphere 2.1: 18-crown-6 ether / dimethyl sulfoxide / 4 h / 100 °C / |Inert atmosphere 3.1: iodine; sodium hydrogencarbonate; water / acetone View Scheme

Yield given. Multistep reaction;