Reacción #725884

Ecuación de reacción

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

→

2

Rendimiento 83.7%

2-(1-Methoxycarbonylethoxy)benzoic acid methyl ester

Rendimiento 83.7%

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturarefluxed for 60 hours
2. 2
   workup.DISTILLATIONAcetone was distilled off
3. 3
   workup.ADDITIONwater (1500 ml) was added
4. 4
   ExtracciónCrude 9 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 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 2 (130 g, 55.6%) as a light yellow syrup. The structure was confirmed with NMR.

Fuente