Ethyl Acrylate → HCID 66747345, compound

HRID 331708Notes

Reaction equation

HRID 331708 reaction equation
[OH-].C([N+](C)(C)C)C1C=CC=CC=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:21]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22]#[N:23])[CH:18]=[CH:19][CH:20]=1.[C:31]([O:35][CH2:36]C)(=[O:34])[CH:32]=C>>[CH3:36][O:35][C:31](=[O:34])[CH2:32][C:21]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:22]#[N:23])[C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([O:14][CH3:13])[CH:16]=1

Participants

4

Reactant 3

HCID 8821Ethyl AcrylateHCID 66854Benzyltrimethylammonium hydroxideHCID 66746775HCID 66746775, compound

Product 1

HCID 66747345HCID 66747345, compound

Procedure

Benzyl trimethylammonium hydroxide (40% in MeOH, 100 μl, 0.22 mmol) was added to a stirred mixture of 2-(3-methoxyphenyl)-3-phenylpropanenitrile (1 g, 4.2 mmol) and ethyl acrylate (0.51 g, 5.1 mmol). After the initial exothermic reaction had subsided the mixture was refluxed for 4 h, cooled to room temperature and extracted three times with DCM. The combined organic layers were washed with water, dried, filtered and evaporated to obtain a pale yellow oil m(CR)=1.06 g that was purified by flash chromatography on 12 g SiO2 using 20% EtOAc in cyclohexane affording 594 mg of product.

Workup

  1. customAfter the initial exothermic reaction
  2. temperaturewas refluxed for 4 h
  3. extractionextracted three times with DCM
  4. washThe combined organic layers were washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customto obtain a pale yellow oil m(CR)=1.06 g that
  9. customwas purified by flash chromatography on 12 g SiO2 using 20% EtOAc in cyclohexane affording 594 mg of product

Sources & evidence

ORD record
ord-92863bd6954944f293f89991391ab81e
Source dataset
uspto-grants-2014_11
Patent number
US08877794B2

Reaction notes

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