Ethyl 2-oxovalerate → 4-HYDROXY-4-METHYL-5-HEXENOIC ACID gamma LACTONE

HRID 254235Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 254235
O=[C:2]([CH2:8]CC)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH:11]([Mg]Br)=[CH2:12]>C1COCC1>[CH3:7][C:6]1([CH:11]=[CH2:12])[O:5][C:3](=[O:4])[CH2:2][CH2:8]1

Komponenten

4

Edukt 2

HCID 123521Ethyl 2-oxovalerateHCID 178418507HCID 178418507, Verbindung

Produkt 1

HCID 1025504-HYDROXY-4-METHYL-5-HEXENOIC ACID gamma LACTONEAusbeute 53,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2-ketopentanoate (10 mL, 71 mmol) in 100 mL of THF at −78° C. was added dropwise a solution of 1.0 M vinyl magnesium bromide (80 mL, 80 mmol). After completion of the addition, the mixture was stirred for two more hours, the cooling bath was removed and the mixture was gradually warmed to ambient temperature. After the removal of the most of the solvent, the residue was poured to 2N HCl aqueous solution, extracted with ethyl acetate and dried over MgSO4. Purification by lash column chromatography on silica gel with DCM as elute afforded 4.80 grams of 5-methyl-5-vinyl-dihydro-furan-2-one. 1H-NMR (300 MHz, CDCl3) δ (ppm): 5.824-5.917 (dd, 1H); 5.29 (d, 1H); 5.13 (d, 1H); 2.50-2.56 m, (2H); 2.07-2.18 (m, 2H); 1.48 (s, 3H).

Aufarbeitung

  1. additionAfter completion of the addition
  2. customthe cooling bath was removed
  3. customAfter the removal of the most of the solvent
  4. additionthe residue was poured to 2N HCl aqueous solution
  5. extractionextracted with ethyl acetate
  6. dry with materialdried over MgSO4
  7. customPurification by lash column chromatography on silica gel with DCM
  8. washas elute

Quellen und Nachweise

ORD-Eintrag
ord-bf75d2d060164d01b7d93ce6a7fb772f
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07875607B2

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