Tetrahydrofuran → Ethyl gamma-cyano-gamma-[3-(trifluoromethyl)phenyl]-4-morpholinebutanoate

HRID 903453Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 903453
[F:1][C:2]([F:19])([F:18])[C:3]1[CH:4]=[C:5]([CH:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1.O1CCCC1.[C:25]([O:29][CH2:30][CH3:31])(=[O:28])[CH:26]=[CH2:27]>[OH-].[K+].C(O)C>[C:10]([C:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:18])[F:19])[CH:4]=1)([N:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1)[CH2:27][CH2:26][C:25]([O:29][CH2:30][CH3:31])=[O:28])#[N:11]

Komponenten

6

Edukt 3

HCID 8028TetrahydrofuranHCID 8821Ethyl Acrylate2×HCID 36941922-Morpholino-2-[3-(trifluoromethyl)phenyl]acetonitrile

Produkt 1

HCID 12449509Ethyl gamma-cyano-gamma-[3-(trifluoromethyl)phenyl]-4-morpholinebutanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 14797Potassium HydroxideKatalysator2×HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

To a solution of 5.0 g. of α-[3-(trifluoromethyl)phenyl]-4-morpholineacetonitrile in 200 ml. of tetrahydrofuran stirred at room temperature is added 30 drops of 30% potassium hydroxide in ethanol. To the mixture is added 10 ml. of ethyl acrylate. After one hour an additional 30 drops of 30% potassium hydroxide in ethanol and 10 ml. of ethyl acrylate is added. The mixture is stirred for 2 hours and the solvent removed under vacuum. Toluene is added several times and the solvent removed. The residue is stirred with ether, filtered and the solvent evaporated to give ethyl γ-cyano-γ-[3-(trifluoromethyl)phenyl]-4-morpholinebutanoate (5.6 g.) as an oil. The oil is heated with 70% glacial acetic acid for 2 hours and the solvent removed. The residue is dissolved in dichloromethane and washed with water. The organic layer is dried (Na2SO4) and the solvent removed to give an oil. A mixture of the oil and 300 ml. of 6 N hydrochloric acid is refluxed for 5 hours, cooled and extracted with dichloromethane. The organic layer is extracted with sodium bicarbonate. The aqueous layer is acidified with concentrated hydrochloric acid and extracted with dichloromethane. The extract is dried (Na 2 SO4) and the solvent removed. The residue is crystallized from hexane to give 3-[3-trifluoromethylbenzoyl]propionic acid as crystals, mp. 80°-82° C.

Aufarbeitung

  1. additionTo the mixture is added 10 ml
  2. customthe solvent removed under vacuum
  3. additionToluene is added several times
  4. customthe solvent removed
  5. stirringThe residue is stirred with ether
  6. filtrationfiltered
  7. customthe solvent evaporated

Quellen und Nachweise

ORD-Eintrag
ord-61b59cba0d30453cb1025ff577c22699
Quelldatensatz
uspto-grants-1980_10
Patentnummer
US04226775

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