Potassium Carbonate → Coumarin

HRID 9257

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HRID 9257 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

HCID 323Coumarin수율 38%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-de8f73a85c194ba78978de97959b81eb
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091235B2

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