Triethylamine → 1-(4-Methoxycarbonylphenyl)-4-(4-n-pentyloxyphenyl)butane-1,4-dione

HRID 351539

Reaktionsgleichung

Reaktionsgleichung von HRID 351539
[CH2:1]([O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH:15]=[CH2:16])=[O:14])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[CH:17]([C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1)=[O:18].C(N(CC)CC)C>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(O)C>[CH3:26][O:25][C:23]([C:22]1[CH:27]=[CH:28][C:19]([C:17](=[O:18])[CH2:16][CH2:15][C:13]([C:10]2[CH:9]=[CH:8][C:7]([O:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:12][CH:11]=2)=[O:14])=[CH:20][CH:21]=1)=[O:24]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 15294Methyl 4-FormylbenzoateHCID 227132221-(4-n-Pentyloxyphenyl)acrolein

Produkt 1

HCID 227132231-(4-Methoxycarbonylphenyl)-4-(4-n-pentyloxyphenyl)butane-1,4-dioneAusbeute 81,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chlorideKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A suspension of 1-(4-n-pentyloxyphenyl)acrolein (2.38 g), methyl 4-formylbenzoate (1.97 g), 3-benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chloride and triethylamine (0.91 ml) in ethanol (10 ml) was refluxed for 18 hours. After cooling, the solvents were removed under reduced pressure. The solids were taken up in 1N HCl and extracted with dichloromethane. The organic layer was washed successively with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was triturated with diisopropyl ether, collected by filtration and dried under reduced pressure to give 1-(4-methoxycarbonylphenyl)-4-(4-n-pentyloxyphenyl)butane-1,4-dione (3.41 g).

Aufarbeitung

  1. temperaturewas refluxed for 18 hours
  2. temperatureAfter cooling
  3. customthe solvents were removed under reduced pressure
  4. extractionextracted with dichloromethane
  5. washThe organic layer was washed successively with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was triturated with diisopropyl ether
  9. filtrationcollected by filtration
  10. customdried under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1dfc266d3ef0430ca5d5774187bb1e33
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743776B2

Verknüpfte Notizen

Wird geladen…