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

HRID 1909867

反応式

HRID 1909867 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-147052373a9a4f6f922197eb55206b96
出典データセット
uspto-grants-2013_12
特許番号
US08598355B2

関連ノート

読み込み中…