2-Anisidine hydrochloride → 3-(2-Methoxyphenylaminomethylene)tetrahydropyran-2-one

HRID 729081Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 729081
[Na].O[CH:3]=[C:4]1[CH2:9][CH2:8][CH2:7][O:6][C:5]1=[O:10].Cl.[CH3:12][O:13][C:14]1[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=1[NH2:16]>C(O)C>[CH3:12][O:13][C:14]1[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=1[NH:16][CH:3]=[C:4]1[CH2:9][CH2:8][CH2:7][O:6][C:5]1=[O:10]

Komponenten

5

Edukt 3

HCID 86382-Anisidine hydrochlorideHCID 5360545SodiumHCID 679061533-(Hydroxymethylene)-tetrahydropyran-2-one

Produkt 1

HCID 542814473-(2-Methoxyphenylaminomethylene)tetrahydropyran-2-oneAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

The sodium salt of 3-(hydroxymethylene)-tetrahydropyran-2-one (25 g, 0.17 mol) and 2-methoxyaniline hydrochloride (32 g, 0.2 mol) in ethanol (750 ml) were warmed to 70° C. with stirring for 2 hours, then filtered hot. After evaporation of the ethanol, the crude product was taken up in dichloromethane, washed with dilute hydrochloric acid, dried and evaporated. Trituration with ether gave 3-(2-methoxyphenylaminomethylene)tetrahydropyran-2-one (21.5 g, 55%) as a mixture of E and Z isomers, m.p. 85°-100°.

Aufarbeitung

  1. filtrationfiltered hot
  2. customAfter evaporation of the ethanol
  3. washwashed with dilute hydrochloric acid
  4. customdried
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-36fdb4f109c94248b5012f9d2f4ca79c
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05051508

Notizen zur Reaktion

Wird geladen…