Cyclohexanone → 6-(cyclohex-1-enyl)-4H-thieno[3,2-b]pyrrole-2-carboxylic acid

HRID 1442541ノート

反応式

HRID 1442541 の反応式
[S:1]1[C:8]2[CH:7]=[CH:6][NH:5][C:4]=2[CH:3]=[C:2]1[C:9]([O:11]C)=[O:10].[C:13]1(=O)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.CO.C[O-].[Na+]>CO>[C:13]1([C:7]2[C:8]3[S:1][C:2]([C:9]([OH:11])=[O:10])=[CH:3][C:4]=3[NH:5][CH:6]=2)[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]=1

参加物

5

反応物 3

HCID 7967CyclohexanoneHCID 12110979methyl 4H-thieno(3,2-b)pyrrole-2-carboxylateHCID 23694274Sodium methanolate methanol

生成物 1

HCID 586790836-(cyclohex-1-enyl)-4H-thieno[3,2-b]pyrrole-2-carboxylic acid収率 101.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of methyl 4H-thieno[3,2-b]pyrrole-2-carboxylate (12 g, 68 mmol) and cyclohexanone (21 ml, 204 mmol) in methanol (300 ml) was added 28% sodium methoxide methanol solution (100 ml) and the mixture was stirred with heating under reflux for 2 days. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. 6N Hydrochloric acid (100 ml) was added and the precipitated solid was collected by filtration. The solid was washed successively with water (300 ml×5) and n-hexane (300 ml×3), and dried under reduced pressure to give 6-(cyclohex-1-enyl)-4H-thieno[3,2-b]pyrrole-2-carboxylic acid (17 g, yield 100%).

後処理

  1. temperaturewith heating
  2. temperatureunder reflux for 2 days
  3. concentrationconcentrated under reduced pressure
  4. addition6N Hydrochloric acid (100 ml) was added
  5. filtrationthe precipitated solid was collected by filtration
  6. washThe solid was washed successively with water (300 ml×5) and n-hexane (300 ml×3)
  7. customdried under reduced pressure

出典と根拠

ORDレコード
ord-fc9060bee5e3496d850677ddd86912df
出典データセット
uspto-grants-2010_02
特許番号
US07659263B2

反応ノート

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