Acetic Acid → Ethyl 2-benzyl-3-oxopropanoate

HRID 474580

Reaction equation

HRID 474580 reaction equation
[H-].[Na+].[C:3]1([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:16](OCC)=[O:17].C(O)(=O)C>COCCOC>[CH:16]([CH:10]([CH2:9][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8025Ethyl formateHCID 16237Ethyl 3-phenylpropionateHCID 24758Sodium hydride

Product 1

HCID 562571Ethyl 2-benzyl-3-oxopropanoateYield 100%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a suspension of NaH (2.338 g, 58.5 mmol) in DME (20 mL) was added dropwise a solution of ethyl 3-phenylpropanoate (3.2 g, 19.49 mmol) and ethyl formate (6.28 mL, 78 mmol) in DME (20 mL) at room temperature. The reaction mixture was then stirred overnight. It was neutralized with acetic acid (4 mL), then extracted with EtOAc. The organic phase was collected, washed with brine, dried over Na2SO4, filtered, and concentrated affording the crude title compound (4.02 g, 100% yield). LCMS: rt=2.82 and 3.51 min (a mixture of ketone and enol isomer), [M+H+]=207.1

Workup

  1. extractionextracted with EtOAc
  2. customThe organic phase was collected
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d27c5f8e2b6a479abcff3ee799673c13
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Linked notes

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