Citric Acid → 4-(4-chlorobenzyl)-4H-furo[3,2-b]pyrrole-5-carboxylic acid

HRID 1909867

반응식

HRID 1909867 반응식
[H-].[Na+].[O:3]1[C:10]2[CH:9]=[C:8]([C:11]([O:13]C)=[O:12])[NH:7][C:6]=2[CH:5]=[CH:4]1.Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([CH2:16][N:7]2[C:8]([C:11]([OH:13])=[O:12])=[CH:9][C:10]3[O:3][CH:4]=[CH:5][C:6]2=3)=[CH:18][CH:19]=1

참가 물질

6

반응물 4

HCID 311Citric AcidHCID 24758Sodium hydrideHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 5082263methyl 4H-furo[3,2-b]pyrrole-5-carboxylate

생성물 1

HCID 397337984-(4-chlorobenzyl)-4H-furo[3,2-b]pyrrole-5-carboxylic acid수율 41.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of sodium hydride (0.29 g, 55% dispersion in paraffin liquid) and DMF (10 mL) was added methyl 4H-furo[3,2-b]pyrrole-5-carboxylate (0.5 g) under ice-cooling, followed by stirring for 10 minutes and further 1-(bromomethyl)-4-chlorobenzene (0.81 g) was added thereto, followed by stirring at room temperature for 4 hours. To the reaction mixture was added a 10% aqueous citric acid solution (10 mL), followed by extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate: 5/1-3/1) to obtain 4-(4-chlorobenzyl)-4H-furo[3,2-b]pyrrole-5-carboxylic acid (0.35 g).

후처리

  1. temperaturecooling
  2. stirringby stirring at room temperature for 4 hours
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate: 5/1-3/1)

출처 및 근거

ORD 기록
ord-147052373a9a4f6f922197eb55206b96
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598355B2

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