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

HRID 474581Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 474581
[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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-2b941f68c91f4d6d9063cce943645dec
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637536B2

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