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

HRID 1442541노트

반응식

HRID 1442541 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-fc9060bee5e3496d850677ddd86912df
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07659263B2

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