Potassium Carbonate → Coumarin

HRID 9257

Reaktionsgleichung

Reaktionsgleichung von HRID 9257
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](O)=O)=[CH:4][CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.CC(C1C=CC(F)=CC=1O)=O.[C:35](=O)([O-:37])[O-:36].[K+].[K+]>CN(C=O)C.CN(C1C=CN=CC=1)C.O>[O:37]1[C:6]2[CH:7]=[CH:2][CH:3]=[CH:4][C:5]=2[CH:8]=[CH:9][C:35]1=[O:36]

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 15880(4-Chlorophenyl)acetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 27373264'-Fluoro-2'-hydroxyacetophenone

Produkt 1

HCID 323CoumarinAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of 4-chlorophenylacetic acid (11.05 g, 64.8 mmol) in DMF (100 mL) was treated with CDI (13.13 g, 81 mmol) in several portions over about 15 minutes and the mixture was stirred until gas evolution had ceased. 4-Fluoro-2-hydroxyacetophenone (5.0 g, 32.4 mmol) was added followed by potassium carbonate (15.7 g, 113.6 mmol) and 4-DMAP (about 1 g). The reaction mixture was warmed at about 80° C. for about 10 h then cooled to room temperature. Water (200 mL) was added and the aqueous layer was extracted with ethyl acetate. The combined organic layer was concentrated and the crude product was purified by flash chromatography (ethyl acetate/hexanes) to give a yield of about 3.5 g (38%) of a benzopyranone intermediate.

Aufarbeitung

  1. temperaturethen cooled to room temperature
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. concentrationThe combined organic layer was concentrated
  4. customthe crude product was purified by flash chromatography (ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-de8f73a85c194ba78978de97959b81eb
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091235B2

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