Potassium Carbonate → Coumarin

HRID 9257

反応式

HRID 9257 の反応式
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]

参加物

8

反応物 4

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

生成物 1

HCID 323Coumarin収率 38%

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-de8f73a85c194ba78978de97959b81eb
出典データセット
uspto-grants-2006_08
特許番号
US07091235B2

関連ノート

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