Acetic Acid → Ethyl 2-formyl-3-(2,4,6-trifluorophenyl)propanoate

HRID 705824Notes

Reaction equation

HRID 705824 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([F:11])[C:5]=1[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15].[CH:19](OCC)=[O:20].C(O)(=O)C>COCCOC>[CH:19]([CH:13]([CH2:12][C:5]1[C:4]([F:3])=[CH:9][C:8]([F:10])=[CH:7][C:6]=1[F:11])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:20]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 53425006Ethyl 3-(2,4,6-trifluorophenyl)propanoate

Product 1

HCID 86666190Ethyl 2-formyl-3-(2,4,6-trifluorophenyl)propanoateYield 100%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a suspension of NaH (1.240 g, 31.0 mmol) in DME (15 mL) was added dropwise a solution of ethyl 3-(2,4,6-trifluorophenyl)propanoate (1.8 g, 7.75 mmol) and ethyl formate (3.12 mL, 38.8 mmol) in DME (15 mL) at room temperature. The reaction mixture was then stirred overnight. It was neutralized with acetic acid (1.8 mL), then extracted with EA. The organic layer was collected, washed with brine, dried over Na2SO4, filtered, and concentrated to afford the title compound (2.017 g, 100% yield). LCMS: rt=2.98 and 3.67 min, [M+H+]=261.0, as a mixture of ketone (RT=2.98 min) and enol (RT=3.67 min) isomer.

Workup

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

Sources & evidence

ORD record
ord-d15b6be959fb4a85b5e73d4b03d4ac45
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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