Réaction #1833262

Équation de réaction

Dansyl chloride

2-hydroxyethyl acrylate

diisopropylethylamine

→

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

Rendement 56.5%

Solvants

CH2Cl2

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source