Réaction #1994304

Équation de réaction

(2Z,5E)-2-amino-6-(4-chloro-2-fluoro-phenyl)-4-oxo-hexa-2,5-dienoic acid ethyl ester

(2Z,5E)-2-amino-6-(4-chloro-2-fluorophenyl)-4-oxo-hexa-2,5-dienoic acid ethyl ester

→

6-(4-chloro-2-fluorophenyl)-4-oxo-1,4,5,6-tetrahydropyridine-2-carboxylic acid ethyl ester

Solvants

1,4-dioxane

Conditions de réaction

Traitement

1. 1
   Autregave
2. 2
   Autrepurification by silica gel chromatography
3. 3
   Lavageeluting with 40% EtOAc/hexanes, 6-(4-chloro-2-fluorophenyl)-4-oxo-1,4,5,6-tetrahydropyridine-2-carboxylic acid ethyl ester (11; 43 g, 49%, 96% pure by HPLC) as a tan solid

Mode opératoire

Using the procedure of Example 5, (2Z,5E)-2-amino-6-(4-chloro-2-fluoro-phenyl)-4-oxo-hexa-2,5-dienoic acid ethyl ester (7; 88 g, 0.296 mol) in 1,4-dioxane (880 mL) in a 2 liter Parr reactor gave, following purification by silica gel chromatography eluting with 40% EtOAc/hexanes, 6-(4-chloro-2-fluorophenyl)-4-oxo-1,4,5,6-tetrahydropyridine-2-carboxylic acid ethyl ester (11; 43 g, 49%, 96% pure by HPLC) as a tan solid.

Source