반응 #2044999

반응 방정식

methyl 6-bromohexanoate

2-(6-Hydroxy-naphthalen-2-yl)-propionic acid methyl ester

2-(6-Hydroxynaphthalen-2-yl)-propionic acid methyl ester

K2CO3

sodium iodide

→

9

수율 55.6%

6-[6-(1-Methoxycarbonyl-ethyl)-naphthalen-2-yloxy]-hexanoic acid methyl ester

수율 55.6%

용매

acetone

반응 조건

후처리

1. 1
   온도refluxed for 60 hours
2. 2
   workup.DISTILLATIONAcetone was distilled off
3. 3
   workup.ADDITIONwater (1500 ml) was added
4. 4
   추출Crude 9 was extracted into ethyl acetate
5. 5
   건조dried over Na2SO4
6. 6
   workup.DISTILLATIONdistilled
7. 7
   기타purified by column chromatography on silica gel

실험 절차

To a mixture of 2-(6-Hydroxy-naphthalen-2-yl)-propionic acid methyl ester 6 (150 g, 652 mmol), anhydrous K2CO3 (480 gr, 3.473 mol) and sodium iodide (22.5 grams, 150 mmol) in anhydrous acetone (2000 ml) was added methyl 6-bromohexanoate (216 g, 1.033 mol) and refluxed for 60 hours. Acetone was distilled off and water (1500 ml) was added. Crude 9 was extracted into ethyl acetate, dried over Na2SO4, distilled and purified by column chromatography on silica gel using hexane as eluant to give pure 9 (130 g, 55.6%) as a light yellow syrup. The structure was confirmed with NMR.

출처