Reacción #725883

Ecuación de reacción

methyl 2-chloropropionate

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

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

K2CO3

sodium iodide

→

8

Rendimiento 85.0%

2-[6-(1-Methoxycarbonyl-ethoxy)-naphthalen-2-yl]-propionic acid methyl ester

Rendimiento 85.0%

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturarefluxed for 50 hours
2. 2
   workup.DISTILLATIONAcetone was distilled off
3. 3
   workup.ADDITIONwater (1500 ml) was added
4. 4
   ExtracciónCrude 8 was extracted into ethyl acetate
5. 5
   Secadodried over Na2SO4
6. 6
   workup.DISTILLATIONdistilled
7. 7
   Otropurified by column chromatography on silica gel

Procedimiento

To a mixture of 2-(6-Hydroxy-naphthalen-2-yl)-propionic acid methyl ester 7 (150 g, 652 mmol), anhydrous K2CO3 (455 gr, 3.292 mol) and sodium iodide (22.5 grams, 150 mmol) in anhydrous acetone (2000 ml) was added methyl 2-chloropropionate (107.5 g, 877 mmol) and refluxed for 50 hours. Acetone was distilled off and water (1500 ml) was added. Crude 8 was extracted into ethyl acetate, dried over Na2SO4, distilled and purified by column chromatography on silica gel using hexane as eluant to give pure 8 (175 g, 85%) as a light yellow syrup. The structure was confirmed with NMR.

Fuente