Reaction #59447

Reaction equation

HCl

Cesium carbonate

chloroacetonitrile

2-phenylchroman-6-ol

→

(2-phenylchroman-6-yloxy)acetonitrile

Solvents

acetonitrile

Conditions

Workup

1. 1
   TemperatureThe resulting mixture was refluxed for 6 hours
2. 2
   Extractionit was extracted with ethyl acetate
3. 3
   WashThe combined organic layers were washed with water and saturated NaCl-solution
4. 4
   Dryingdried with Na2SO4
5. 5
   OtherThe solvents were evaporated under reduced pressure

Procedure

Cesium carbonate (310 mg) and chloroacetonitrile (62 μl) were added into a solution of 2-phenylchroman-6-ol (200 mg) in acetonitrile (3 ml). The resulting mixture was refluxed for 6 hours. The reaction mixture was allowed to cool to room temperature and 1 M HCl-solution was added and it was extracted with ethyl acetate. The combined organic layers were washed with water and saturated NaCl-solution and dried with Na2SO4. The solvents were evaporated under reduced pressure to give (2-phenylchroman-6-yloxy)acetonitrile. 1H NMR (400 MHz, d6-DMSO) δ: 7.44-7.30 (m, 5H), 6.86-6.81 (m, 3H), 5.08 (dd, 1H, J 9.8, 2.2 Hz), 5.07 (s, 2H), 2.97 (ddd, 1H, J −16.9, 10.9, 6.0. Hz), 2.71 (ddd, 1H, J −16.9, 5.0, 3.4 Hz), 2.15 (m, 1H), 1.97 (m, 1H).

Source