Reacción #1969487

Ecuación de reacción

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

K2CO3

sodium iodide

acetone

→

31

Rendimiento 54.3%

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

Rendimiento 54.3%

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturarefluxed for 6 hours
2. 2
   workup.DISTILLATIONAcetone was distilled
3. 3
   workup.ADDITIONwater (1500 mL) was added
4. 4
   ExtracciónCrude 31 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 30 (175 grams, 761 mmol), anhydrous K2CO3 (315 grams, 2.279 mmol), sodium iodide (21 grams, 140 mmol) in anhydrous acetone (2000 mL) was added methyl Chloro acetate (104 grams, 958 mmol) and refluxed for 6 hours. Acetone was distilled and water (1500 mL) was added. Crude 31 was extracted into Ethyl acetate, dried over Na2SO4, distilled and purified by column chromatography on silica gel using Benzene as eluant to give pure 31 (125 grams, 54.3%) as a pale yellow syrup. The structure was confirmed with NMR. IHNMR (CDCl3) δ 1.57 (d, 3H, CH3), 3.64 (s, 3H, Ester), 3.78 (s, 3H, Ester), 3.80 (q, 1H, CH), 4.70 (s, 1H, Ar), 7.22 (d, 1H, Ar), 7.36 (m, 2H, Ar), 7.68 (m, 3H, Ar).

Fuente