反应 #2044999

反应方程式

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

收率 55.6%

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

收率 55.6%

溶剂

acetone

反应条件

后处理

1. 1
   温度refluxed for 60 hours
2. 2
   workup.DISTILLATIONAcetone was distilled off
3. 3
   workup.ADDITIONwater (1500 ml) was added
4. 4
   萃取Crude 9 was extracted into ethyl acetate
5. 5
   干燥dried over Na2SO4
6. 6
   workup.DISTILLATIONdistilled
7. 7
   其他purified by column chromatography on silica gel

实验过程

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.

来源