Methyl 4-Formylbenzoate → Methyl 4-(2-methoxyethenyl)benzoate

HRID 2261787

Reaktionsgleichung

Reaktionsgleichung von HRID 2261787
CC(C)([O-])C.[K+].[Cl-].[CH3:8][O:9][CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH:30]([C:32]1[CH:41]=[CH:40][C:35]([C:36]([O:38][CH3:39])=[O:37])=[CH:34][CH:33]=1)=O>C1COCC1>[CH3:39][O:38][C:36](=[O:37])[C:35]1[CH:40]=[CH:41][C:32]([CH:30]=[CH:8][O:9][CH3:10])=[CH:33][CH:34]=1

Komponenten

5

Edukt 3

HCID 15294Methyl 4-FormylbenzoateHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 54136641Methyl 4-(2-methoxyethenyl)benzoateAusbeute 80,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To an ambient temperature suspension of potassium tert-butoxide (2.05 g, 18.27 mmol) in THF (60 mL) is added the (methoxymethyl)triphenyl phosphonium chloride (6.26 g, 18.27 mmol). The reaction mixture is stirred at room temperature for 20 min. Solid methyl 4-formylbenzoate (1.0 g, 6.09 mmol) is added and the reaction is stirred at room temperature overnight. The reaction mixture is quenched with saturated aq. NH4Cl and concentrated. The residue is partitioned between Et2O and water. The aqueous layer is extracted with Et2O and the combined organic layers are washed with brine, dried (MgSO4), filtered, concentrated, and chromatographed (0% to 30% EtOAC/Hex) to yield the title compound (939 mg, 80%) as a mix of E/Z isomers.

Aufarbeitung

  1. stirringthe reaction is stirred at room temperature overnight
  2. customThe reaction mixture is quenched with saturated aq. NH4Cl
  3. concentrationconcentrated
  4. customThe residue is partitioned between Et2O and water
  5. extractionThe aqueous layer is extracted with Et2O
  6. washthe combined organic layers are washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customchromatographed (0% to 30% EtOAC/Hex)

Quellen und Nachweise

ORD-Eintrag
ord-700444a7c81b4b9faf7ceb5b8ab3e0d9
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07846960B2

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