5-[2-(3-Ethylphenyl)ethyl]-2-methyloxazole-4-carboxylic acid → 7-Ethyl-9,10-dihydro-2-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-one

HRID 324462

Reaktionsgleichung

Reaktionsgleichung von HRID 324462
[CH2:1]([C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][C:11]2[O:15][C:14]([CH3:16])=[N:13][C:12]=2[C:17]([OH:19])=O)[CH:6]=[CH:7][CH:8]=1)[CH3:2]>S(Cl)(Cl)=O>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]2[C:17](=[O:19])[C:12]3[N:13]=[C:14]([CH3:16])[O:15][C:11]=3[CH2:10][CH2:9][C:5]=2[CH:4]=1)[CH3:2]

Komponenten

3

Edukt 1

HCID 220036405-[2-(3-Ethylphenyl)ethyl]-2-methyloxazole-4-carboxylic acid

Produkt 1

HCID 220035847-Ethyl-9,10-dihydro-2-methyl-4H-benzo[5,6]cyclohepta[1,2-d]oxazol-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

A solution of the product from step (vii) (9.5 g) in thionyl chloride (100 ml) was stirred at room temperature for 4 days. After removal of solvent under reduced pressure, the residue was dissolved in 1,2-dichloroethane (200 ml) and treated with aluminium chloride (23 g). The reaction mixture was heated at reflux for 1 hour and allowed to cool. The resultant suspension was partitioned between 10% hydrochloric acid and dichloromethane. The combined extracts were evaporated, triturated with acetonitrile, and filtered through a plug of celite. Evaporation afforded a residue which was purified by chromatography eluting with 50-100% ethyl acetate in isohexane.

Aufarbeitung

  1. customAfter removal of solvent under reduced pressure
  2. dissolutionthe residue was dissolved in 1,2-dichloroethane (200 ml)
  3. additiontreated with aluminium chloride (23 g)
  4. temperatureThe reaction mixture was heated
  5. temperatureat reflux for 1 hour
  6. temperatureto cool
  7. customThe resultant suspension was partitioned between 10% hydrochloric acid and dichloromethane
  8. customThe combined extracts were evaporated
  9. customtriturated with acetonitrile
  10. filtrationfiltered through a plug of celite
  11. customEvaporation
  12. customafforded a residue which
  13. customwas purified by chromatography
  14. washeluting with 50-100% ethyl acetate in isohexane

Quellen und Nachweise

ORD-Eintrag
ord-439642bca3914b95b6b9a3dedface89f
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06218376B1

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