تفاعل #1833263

معادلة التفاعل

2-hydroxyethyl acrylate

1-naphthoic acid

EDC

→

naphthalene-1-carbonyloxy-2-ethyl acrylate

المردود 82.3%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر