Dimethylformamide → Methyl 4-[4-(5,8-dimethylnaphthalene-2-yl)-4-oxo-butanoyl]benzoate

HRID 277173Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 277173
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH:13]=[O:14])=[CH:7]2.[C:15]([C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1)(=[O:18])[CH:16]=[CH2:17].C(N(CC)CC)C.CN(C)C=O>O>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([C:13](=[O:14])[CH2:17][CH2:16][C:15]([C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1)=[O:18])=[CH:7]2

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 10774024Methyl 4-acryloyl-benzoateHCID 144876095,8-Dimethyl-2-naphthaldehyde

Produkt 1

HCID 15487489Methyl 4-[4-(5,8-dimethylnaphthalene-2-yl)-4-oxo-butanoyl]benzoateAusbeute 40,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of 1.0 g of 5,8-dimethyl-2-naphthaldehyde, 1.2 g of methyl 4-acryloyl-benzoate, 0.28 g of 3-benzyl-5-(2-hydroxymethyl)-4-methylthiazolium chloride, 0.88 ml triethylamine and 20 ml N,N-dimethylformamide was heated under stirring at 70° C. for 3 hours. After the reaction solution was left standing for cooling to room temperature, water was added thereto, and the reaction solution was extracted with ethyl acetate (20 ml×3). The organic layers were combined, washed with brine, dried over anhydrous magnesium sulfate and filtered. Then, the filtrate was concentrated and the resulting crude crystals were washed with a mixed solvent of n-hexane and ethyl acetate to give 0.82 g of the title compound as colorless crystals.

Aufarbeitung

  1. temperaturewas heated
  2. waitAfter the reaction solution was left
  3. temperaturefor cooling to room temperature
  4. extractionthe reaction solution was extracted with ethyl acetate (20 ml×3)
  5. washwashed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationThen, the filtrate was concentrated
  9. washthe resulting crude crystals were washed with a mixed solvent of n-hexane and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-846f97dcc71e43768acfd60278ef6283
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355669B1

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