Triethyl phosphonoacetate → (2E)-3-(2,6-Difluoro-4-methoxyphenyl)-2-propenoic Acid Ethyl Ester

HRID 2110842Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2110842
C(OP([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[F:17][C:18]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([F:28])[C:19]=1[CH:20]=O>O1CCCC1.C(OCC)(=O)C>[F:17][C:18]1[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[C:22]([F:28])[C:19]=1/[CH:20]=[CH:9]/[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Komponenten

6

Edukt 3

HCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 37037132,6-Difluoro-4-methoxybenzaldehyde

Produkt 1

HCID 57636644(2E)-3-(2,6-Difluoro-4-methoxyphenyl)-2-propenoic Acid Ethyl EsterAusbeute 52,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of ethyl diethylphosphonoacetate (2.34 g, 10.4 mmol) and sodium hydride (60% in oil, 0.38 g, 9.50 mmol) in tetrahydrofuran (40 mL) was stirred under ice-cooling for 10 min. 2,6-Difluoro-4-methoxybenzaldehyde (1.5 g, 8.71 mmol) was added to the solution, and the mixture was stirred for 4 hr while raising the temperature to room temperature. The reaction mixture was diluted with ethyl acetate, and the mixture washed successively with aqueous citric acid solution, water and aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:10-1:5) to give the title compound (1.1 g, yield 52%) as colorless needle crystals. MS: m/z 243 (MH+).

Aufarbeitung

  1. temperaturecooling for 10 min
  2. washthe mixture washed successively with aqueous citric acid solution, water and aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3054b3eb97e0463797f390fd5926faf9
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07517910B2

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