Acetic Acid → Ethyl 3-(4-cyanophenyl)-2-formylpropanoate

HRID 474579Notes

Reaction equation

HRID 474579 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][CH:6]=1)#[N:4].[CH:18](OCC)=[O:19].C(O)(=O)C>COCCOC.CC(=O)OCC>[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH:12]([CH:18]=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][CH:6]=1)#[N:4]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 11435631Ethyl 3-(4-cyanophenyl)propanoate

Product 1

HCID 86666189Ethyl 3-(4-cyanophenyl)-2-formylpropanoateYield 82%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of NaH (1.102 g, 27.6 mmol) in DME (15 mL) was added dropwise a solution of ethyl 3-(4-cyanophenyl)propanoate (1.4 g, 6.89 mmol) and ethyl formate (2.77 mL, 34.4 mmol) in DME (15 mL). The reaction mixture was then stirred at room temperature overnight. It was neutralized with acetic acid (1.7 mL), then extracted with EtOAc. The organic phases were collected, washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified by a flash column chromatography, eluting with PE:EA=2:1, to give the title compound as a pale yellow oil (1.3 g, 82% yield). LCMS: rt=2.47 and 3.13 min (a mixture of ketone and enol isomer), [M+H+]=232.2

Workup

  1. extractionextracted with EtOAc
  2. customThe organic phases were collected
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by a flash column chromatography
  8. washeluting with PE

Sources & evidence

ORD record
ord-72a847b463ee49a2b6099cf6f9f92aed
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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