Benzaldehyde → 3-Butyl-5-([E]-styryl)-isoxazole-4-carboxylic acid

HRID 1695453Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1695453
C([O:3][C:4]([C:6]1[C:7]([CH2:12][CH2:13][CH2:14][CH3:15])=[N:8][O:9][C:10]=1[CH3:11])=[O:5])C.[CH:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[O-]CC.[Na+].Cl>C(O)C>[CH2:12]([C:7]1[C:6]([C:4]([OH:3])=[O:5])=[C:10](/[CH:11]=[CH:16]/[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[O:9][N:8]=1)[CH2:13][CH2:14][CH3:15]

Komponenten

6

Edukt 4

HCID 240BenzaldehydeHCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 665992233-Butyl-5-methyl-isoxazole-4-carboxylic acid ethyl ester

Produkt 1

HCID 666437323-Butyl-5-([E]-styryl)-isoxazole-4-carboxylic acidAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 3-butyl-5-methyl-isoxazole-4-carboxylic acid ethyl ester (15.0 g, 71.0 mmol) and benzaldehyde (7.2 mL, 71.0 mmol) in ethanol (100 mL) was added sodium ethoxide solution (21% in ethanol, 29.1 mL, 78.0 mmol) and the reaction mixture was stirred at reflux for 2 h, cooled to room temperature and stirred for 17 h. Hydrochloric acid (1 N, 85 mL) was added and the resulting mixture was extracted twice with dichloromethane. The combined phases were washed with brine, dried over sodium sulfate and filtered. The filtrate was concentrated to a bright yellow pasty solid and recrystallized from hot heptane/ethyl acetate to afford the title compound (8.0 g, 42%) as a yellow solid. MS: m/e=270.4 [M−H]−.

Aufarbeitung

  1. temperatureat reflux for 2 h
  2. stirringstirred for 17 h
  3. extractionthe resulting mixture was extracted twice with dichloromethane
  4. washThe combined phases were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated to a bright yellow pasty solid
  8. customrecrystallized from hot heptane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-d1a12e477eec4ffd92a969313bb8b586
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163728B2

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