反応 #1833262

反応方程式

Dansyl chloride

2-hydroxyethyl acrylate

diisopropylethylamine

→

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

収率 56.5%

溶媒

CH2Cl2

反応条件

後処理

1. 1
   その他The reaction was quenched with a 5% solution of NH4Cl
2. 2
   抽出extracted (3×20 ml) with CH2Cl2
3. 3
   乾燥The combined organic layers were dried over anhydrous MgSO4
4. 4
   その他purified with column chromatography on silica gel (1:4, EtOAc:hexanes)

実験手順

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.

出典