Acetic Acid → HCID 57809776, Verbindung

HRID 2106053Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2106053
[CH2:1]([O:3][P:4]([CH:9]([F:11])[F:10])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[Li+].CC([N-]C(C)C)C.[CH3:20][C:21]([C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=1[O:33][CH3:34])([CH3:25])[CH2:22][CH:23]=[O:24].C(O)(=O)C>C1COCC1.C(OCC)(=O)C>[CH2:1]([O:3][P:4]([C:9]([F:11])([F:10])[CH:23]([OH:24])[CH2:22][C:21]([C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=1[O:33][CH3:34])([CH3:25])[CH3:20])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 2724682Lithium diisopropylamideHCID 2758305Phosphonic acid, (difluoromethyl)-, diethyl esterHCID 578098963-(5-Fluoro-2-methoxyphenyl)-3-methylbutyraldehyde

Produkt 1

HCID 57809776HCID 57809776, VerbindungAusbeute 64,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of the difluoromethylphosphonic acid diethyl ester (1.35 g) in THF (5.0 mL) cooled in a dry ice/acetone bath was added LDA (5.0 mL, 1.5M in cyclohexane) dropwise over 5.0 minutes. After 10.0 minutes, a solution of 3-methyl-3-(2-methoxy-5-fluorophenyl)butyraldehyde (0.94 g) in THF (5.0 mL) was added dropwise. After an additional 20.0 minutes, acetic acid (1 mL) was added and the mixture was warmed to room temperature. The mixture was diluted with ethyl acetate, washed with water, dried, filtered, and evaporated in vacuo. Fractionation of the residue over silica gel (eluent: methylene chloride-ethyl acetate (1:4)) gave the desired [1,1-difluoro-4-(5-fluoro-2-methoxyphenyl)-2-hydroxy-4-methylpentyl]phosphonic acid diethyl ester (1.15 g, 40%) as an oil that crystallized on treatment with hexanes.

Aufarbeitung

  1. waitAfter an additional 20.0 minutes
  2. washwashed with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4b89ccc07ad040a295b19a2e79a8252d
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07579469B2

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