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Potassium Carbonate → HCID 178458881, Verbindung

HRID 703362
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 703362
[OH:1][C:2]1[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][C:11]([SH:14])=[CH:10][CH:9]=2)[CH2:5][C:4](=[O:15])[C:3]=1[C:16](=[O:19])[CH2:17][CH3:18].F[C:21]1[C:26]([F:27])=[CH:25][C:24]([C:28]([F:31])([F:30])[F:29])=[CH:23][N:22]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O.C(Cl)Cl>[C:16]([C:3]1[C:2](=[O:1])[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14][C:21]3[C:26]([F:27])=[CH:25][C:24]([C:28]([F:31])([F:29])[F:30])=[CH:23][N:22]=3)=[CH:10][CH:9]=2)[CH2:5][C:4]=1[OH:15])(=[O:19])[CH2:17][CH3:18]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 134215472,3-Difluoro-5-(trifluoromethyl)pyridineHCID 178458882HCID 178458882, Verbindung

Produkt 1

HCID 178458881HCID 178458881, VerbindungAusbeute 89,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel
HCID 6342
Acetonitrile
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 4.0 g (0.0145 mol) of 3-hydroxy-5-(4-mercaptophenyl)-2-propionyl-cyclohex-2-en-1-one in 50 mL of acetonitrile was added 3.90 g (0.0212 mol) of 2,3-difluoro-5-(trifluoromethyl)pyridine and 4.50 g (0.0326 mol) of powdered potassium carbonate. The mixture was stirred one hour at ambient temperature and then heated at reflux for 1.5 hours and cooled to room temperature. The reaction mixture was diluted with 150 mL of water and 150 mL of methylene chloride. The organic layer was separated, washed twice with 150 mL portions of water and dried over Na2SO4. The solvent was removed in vacuo leaving 5.7 g of the crude product which was purified by column chromatography using methylene chloride as the eluent. Recrystallization of the crude from ethanol gave the above named product in a yield of 2.25 g (35 percent of theoretical). The product melted at 152°-154° C.; 1H NMR (CDCl3): δ 1.10 (t, 3H, CH3CH2 --), 2.55-3.65 (m, 7H, ring protons and CH3CH2 --), 7.15-8.50 (m, 6H, ArH), 18.2 (s, 1H, OH).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 1.5 hours
  3. temperaturecooled to room temperature
  4. customThe organic layer was separated
  5. washwashed twice with 150 mL portions of water
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-595bb586452c4d119203a00a416e7987
Quelldatensatz
uspto-grants-1991_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04983211

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