Réaction #2045002

Équation de réaction

Capsaicin

K2CO3

sodium iodide

disodium phosphate

methyl 6-bromohexanoate

→

12

Rendement 52.8%

6-{2-Methoxy-4-[(8-methyl-non-6-enoylamino)-methyl]-phenoxy}-hexanoic acid methyl ester

Rendement 52.8%

Solvants

acetone

Conditions de réaction

Traitement

1. 1
   Températurerefluxed for 24 hours
2. 2
   workup.DISTILLATIONAcetone was distilled off
3. 3
   workup.ADDITIONwater (15 ml) was added
4. 4
   FiltrationCrude 12 was filtered
5. 5
   Autredried
6. 6
   Autrepurified by column chromatography on silica gel

Mode opératoire

To a mixture of Capsaicin (2 g, 6.56 mmol), anhydrous K2CO3 (3 g, 22 mmol), sodium iodide (2 g, 13.3 mmol) and disodium phosphate (2 g, 14.2 mmol) in anhydrous acetone (50 ml) was added methyl 6-bromohexanoate (2 g, 9.6 mmol) and refluxed for 24 hours. Acetone was distilled off and water (15 ml) was added. Crude 12 was filtered, dried and purified by column chromatography on silica gel using benzene:ethyl acetate (9:1) to give pure 12 (1.5 g, 52.8%) as a pale white powder. The melting point was found to be 69.2-70.8° C.

Source