反応 #2045002

反応方程式

Capsaicin

K2CO3

sodium iodide

disodium phosphate

methyl 6-bromohexanoate

→

12

収率 52.8%

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

収率 52.8%

溶媒

acetone

反応条件

後処理

1. 1
   温度refluxed for 24 hours
2. 2
   workup.DISTILLATIONAcetone was distilled off
3. 3
   workup.ADDITIONwater (15 ml) was added
4. 4
   ろ過Crude 12 was filtered
5. 5
   その他dried
6. 6
   その他purified by column chromatography on silica gel

実験手順

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.

出典