반응 #2045002

반응 방정식

Capsaicin

K2CO3

sodium iodide

disodium phosphate

methyl 6-bromohexanoate

→

12

수율 52.8%

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

수율 52.8%

용매

acetone

반응 조건

후처리

1. 1
   온도refluxed for 24 hours
2. 2
   workup.DISTILLATIONAcetone was distilled off
3. 3
   workup.ADDITIONwater (15 ml) was added
4. 4
   여과Crude 12 was filtered
5. 5
   기타dried
6. 6
   기타purified by column chromatography on silica gel

실험 절차

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.

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