2-Pyrrolidone → 3-(3,5-Di-tert-butyl-4-hydroxybenzylidene)-2-pyrrolidone

HRID 2295077Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2295077
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].C(=O)([O-])OC.[Mg+2].COC(=O)[O-].[C:18]([C:22]1[CH:23]=[C:24]([CH:27]=[C:28]([C:31]([CH3:34])([CH3:33])[CH3:32])[C:29]=1[OH:30])[CH:25]=O)([CH3:21])([CH3:20])[CH3:19]>CN(C=O)C>[CH3:21][C:18]([C:22]1[CH:23]=[C:24]([CH:25]=[C:3]2[CH2:4][CH2:5][NH:1][C:2]2=[O:6])[CH:27]=[C:28]([C:31]([CH3:34])([CH3:33])[CH3:32])[C:29]=1[OH:30])([CH3:19])[CH3:20]

Komponenten

5

Edukt 3

HCID 120252-PyrrolidoneHCID 732193,5-Di-tert-butyl-4-hydroxybenzaldehydeHCID 167017Carbonic acid, monomethyl ester, magnesium salt (2:1)

Produkt 1

HCID 538962973-(3,5-Di-tert-butyl-4-hydroxybenzylidene)-2-pyrrolidoneAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, 1.52 ml of 2-pyrrolidinone was added to a solution of 32 ml of 2M magnesium methyl carbonate in DMF and 5.86 g of 3,5-di-tert-butyl-4-hydroxybenzaldehyde. The resultant mixture was stirred at reflux temperature for six days and then allowed to cool. The cooled reaction mixture was poured into 40 g of ice containing 10 ml concentrated hydrochloric acid and then extracted with chloroform. The chloroform layer was collected, filtered and the filtrate was concentrated. The resulting residue was purified by silica gel chromatography and recrystallized from ethyl acetate to give the desired titled product (21% yield), m.p. 216°-218° C.

Aufarbeitung

  1. temperatureat reflux temperature for six days
  2. temperatureto cool
  3. customThe cooled reaction mixture
  4. extractionextracted with chloroform
  5. customThe chloroform layer was collected
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customThe resulting residue was purified by silica gel chromatography
  9. customrecrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-296030aa32fc4ead986d02eff9b38505
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05691367

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