Reacción #1833263

Ecuación de reacción

2-hydroxyethyl acrylate

1-naphthoic acid

EDC

→

naphthalene-1-carbonyloxy-2-ethyl acrylate

Rendimiento 82.3%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was quenched with a 5% solution of NH4Cl
2. 2
   Lavadothe mixture was washed with water
3. 3
   ExtracciónAfter extraction with EtOAc (3×20 ml)
4. 4
   Secadothe organic layers were dried over anhydrous MgSO4
5. 5
   Otropurified with column chromatography on silica gel (1:4, EtOAc:hexanes)

Procedimiento

To a solution of 2-hydroxyethyl acrylate (1.01 g, 8.7 mmol) and 1-naphthoic acid (1.00 g, 5.8 mmol) in 10 ml of freshly distilled CH2Cl2 was added EDC (1.60 g, 8.7 mmol) and DMAP (cat. amount) at room temperature. The resultant mixture was stirred at room temperature until TLC indicated the disappearance of starting material. The reaction was quenched with a 5% solution of NH4Cl and the mixture was washed with water. After extraction with EtOAc (3×20 ml), the organic layers were dried over anhydrous MgSO4 and purified with column chromatography on silica gel (1:4, EtOAc:hexanes) to give 1.29 g (82%) of naphthalene-1-carbonyloxy-2-ethyl acrylate as a colorless oil. 1H NMR (250 MHz) δ 8.91 (d, J=8.4 Hz, 1H), 8.21 (d, J=7.1 Hz, 1H), 8.04 (d, J=8.2 Hz, 1H), 7.90 (d, J=8.0 Hz, 1H), 7.57 (m, 3H), 6.49 (d, J=17.3 Hz, 1H), 6.19 (dd, J=17.3, 10.4 Hz, 1H), 5.71 (d, J=10.4 Hz, 1H), 4.66 (m, 2H), 4.58 (m, 2H). 13C NMR (63 MHz) δ 167.2, 165.9, 133.8, 133.6, 131.5, 131.3, 130.5, 128.6, 128.0, 127.8, 126.6, 126.2, 125.7, 124.5, 62.7, 62.3.

Fuente