Hydrochloric Acid → (2-Phenylchroman-6-yloxy)acetonitrile

HRID 31169Notes

Reaction equation

HRID 31169 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:8][C:9]#[N:10].[C:11]1([CH:17]2[CH2:26][CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([OH:27])[CH:23]=3)[O:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>C(#N)C>[C:11]1([CH:17]2[CH2:26][CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([O:27][CH2:8][C:9]#[N:10])[CH:23]=3)[O:18]2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7856ChloroacetonitrileHCID 10796Cesium carbonateHCID 212875382-Phenylchroman-6-ol

Product 1

HCID 17978606(2-Phenylchroman-6-yloxy)acetonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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).

Workup

  1. temperatureThe resulting mixture was refluxed for 6 hours
  2. extractionit was extracted with ethyl acetate
  3. washThe combined organic layers were washed with water and saturated NaCl-solution
  4. dry with materialdried with Na2SO4
  5. customThe solvents were evaporated under reduced pressure

Sources & evidence

ORD record
ord-3b37b6fb8c49401996cc4e8d9f00f8f6
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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