반응 #59445

반응 방정식

Cesium carbonate

2-(dimethylamino)ethyl chloride

2-phenylchroman-6-ol

→

Dimethyl[2-(2-phenylchroman-6-yloxy)ethyl]amine

용매

ethyl acetate

acetonitrile

반응 조건

후처리

1. 1
   온도The reaction mixture was refluxed for 30 minutes
2. 2
   기타After removing the solvents
3. 3
   추출extracted with ethyl acetate
4. 4
   세척The combined organic layers were washed with water
5. 5
   건조with saturated NaCl-solution and dried with Na2SO4
6. 6
   기타The dimethyl[2-(2-phenylchroman-6-yloxy)-ethyl]amine was crystallised from heptane

실험 절차

Cesium carbonate (230 mg) and an excess of 2-(dimethylamino)ethyl chloride in ethyl acetate were added into a solution of 2-phenylchroman-6-ol (150 mg) in acetonitrile (5 ml). The reaction mixture was refluxed for 30 minutes. After removing the solvents, the residue was taken up in water and extracted with ethyl acetate. The combined organic layers were washed with water and then with saturated NaCl-solution and dried with Na2SO4. The dimethyl[2-(2-phenylchroman-6-yloxy)-ethyl]amine was crystallised from heptane. 1H NMR (400 MHz, d6-DMSO) δ: 7.43-7.30 (m, 5H), 6.75-6.67 (m, 3H), 5.03 (dd, 1H, J 10.0, 2.2 Hz), 3.95 (t, 2H, J 5.9 Hz), 2.94 (ddd, 1H, J −16.7, 10.9, 5.8 Hz), 2.69 (ddd, 1H, J −16.7, 5.2, 3.3 Hz), 2.58 (t, 2H, J 5.9 Hz), 2.13 (m, 1H), 1.96 (m, 1H).

출처