Morpholine → Ethyl 2,4-dimethyl[1,1'-biphenyl]-3-carboxylate

HRID 1153842

Reaktionsgleichung

Reaktionsgleichung von HRID 1153842
[CH3:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([CH3:13])OC(=O)[CH:3]=1.[C:15]1([CH:21]=[CH:22]N2CCOCC2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.N1CCOCC1>C1(C)C=CC=CC=1>[CH3:13][C:6]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:2]([CH3:3])[CH:1]=[CH:22][C:21]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Komponenten

5

Edukt 3

HCID 8083MorpholineHCID 76918ethyl 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylateHCID 544920984-(2-Phenylethenyl)morpholine

Produkt 1

HCID 13126289Ethyl 2,4-dimethyl[1,1'-biphenyl]-3-carboxylateAusbeute 18,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

Under a dry nitrogen atmosphere a solution of commercial ethyl 4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate (19.6 g, 0.1 mole) in toluene (20 ml) was added dropwise to a stirred solution of 4-(2-phenylethenyl)morpholine (14.3 g, 0.076 mole) in toluene (200 ml). Preparation of the morpholine derivative is described in U.S. Pat. No. 3,922,237. After the addition, the reaction mixture was heated at reflux for approximately 20 hours. The reaction mixture was then cooled and concentrated under reduced pressure, leaving a residue. The residue was heated at 170° under a dry nitrogen atmosphere for 3.5 hours, allowed to cool to room temperature, and then filtered. The filtrate was purified by column chromatography on silica gel, elution first with n-hexane: ethyl acetate, and finally ethyl acetate, to give ethyl 2,4-dimethyl-[1,1'-biphenyl]-3-carboxylate (3.5 g) as a yellow oil.

Aufarbeitung

  1. additionAfter the addition
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for approximately 20 hours
  4. temperatureThe reaction mixture was then cooled
  5. concentrationconcentrated under reduced pressure
  6. customleaving a residue
  7. temperatureThe residue was heated at 170° under a dry nitrogen atmosphere for 3.5 hours
  8. filtrationfiltered
  9. customThe filtrate was purified by column chromatography on silica gel, elution first with n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-e52eceddde834449b16106a075d0035c
Quelldatensatz
uspto-grants-1984_12
Patentnummer
US04486588

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