Acetic Acid → HCID 19895670, Verbindung

HRID 892512Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 892512
[CH3:1][C:2]1([CH3:19])[CH:7]=[C:6]([C:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][N:9]=2)[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[O:3]1.C(O)(=O)C>C(O)C.[Pd]>[CH3:1][C:2]1([CH3:19])[CH2:7][CH:6]([C:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][N:9]=2)[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[O:3]1

Komponenten

5

Edukt 2

HCID 176Acetic AcidHCID 19895692HCID 19895692, Verbindung

Produkt 1

HCID 19895670HCID 19895670, VerbindungAusbeute 46,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

2.97 g of 2,2-dimethyl-4-(3-methyl-2-pyridyl)-2H-1-benzopyran were dissolved in 50 ml of ethanol and shaken at room temperature under a hydrogen atmosphere with 10% palladium-on-charcoal in the presence of 0.5 ml of acetic acid. After 24 hours the catalyst was filtered off and the filtrate was evaporated. The residue was chromatographed on silica gel using ethyl acetate/petroleum ether (1:4) for the elution. There were obtained 1.4 g of 3,4-dihydro-2,2-dimethyl-4-(3-methyl-2-pyridyl)-2H-1-benzopyran together with mixed fractions containing this compound and starting material. The procedure described above was carried out on the mixed fractions to give 675 mg of 3,4-dihydro-2,2-dimethyl-4-(3-methyl-2-pyridyl)-2H-1-benzopyran which was recrystallized from t-butyl methyl ether and then melted at 100°-102° C.

Aufarbeitung

  1. filtrationAfter 24 hours the catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residue was chromatographed on silica gel
  4. washfor the elution

Quellen und Nachweise

ORD-Eintrag
ord-7eaa6eb285e84619a5406d0f04253c5b
Quelldatensatz
uspto-grants-1992_06
Patentnummer
US05118694

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