تفاعل #1833262

معادلة التفاعل

Dansyl chloride

2-hydroxyethyl acrylate

diisopropylethylamine

→

2-(5-dimethylamino-naphthalene-1-sulfonyloxy)-ethyl acrylate

المردود 56.5%

المذيبات

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction was quenched with a 5% solution of NH4Cl
2. 2
   استخلاصextracted (3×20 ml) with CH2Cl2
3. 3
   تجفيفThe combined organic layers were dried over anhydrous MgSO4
4. 4
   أخرىpurified with column chromatography on silica gel (1:4, EtOAc:hexanes)

الإجراء التجريبي

To a solution of 2-hydroxyethyl acrylate (25.8 mg, 0.2 mmol) in 2 ml of freshly distilled CH2Cl2 was added diisopropylethylamine (DIPEA, 0.35 ml, 0.2 mmol) dropwise at 0° C. Dansyl chloride (50.0 mg, 0.19 mmol) was then added dropwise, and 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 extracted (3×20 ml) with CH2Cl2. The combined organic layers were dried over anhydrous MgSO4 and purified with column chromatography on silica gel (1:4, EtOAc:hexanes) to give 37.5 mg (56%) of 2-(5-dimethylamino-naphthalene-1-sulfonyloxy)-ethyl acrylate as a yellow semi solid. 1H NMR (250 MHz) δ 8.61 (d, J=8.6 Hz, 1H), 8.26 (t, J=6.3 Hz, 2H), 7.56 (m, 2H), 7.20 (d, J=7.7 Hz, 1H), 6.19 (dd, J=16.5, 2.5 Hz, 1H), 5.80 (dd, J=16.5, 10.3 Hz, 1H), 5.71 (dd, J=16.5, 10.3 Hz, 1H), 4.25 (m, 4H), 2.88 (s, 6H). 13C NMR (63 MHz) δ 158.0, 151.7, 131.8, 131.5, 130.9, 130.6, 129.8, 128.8, 127.3, 123.0, 119.4, 115.6, 67.8, 61.5, 45.4.

المصدر