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Hydrochloric Acid → 3-[2,2′-Bithiophen]-5-yl-2-propenoic acid

HRID 1289131
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HRID 1289131 반응식
[CH:1]([C:3]1[S:7][C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[CH:5][CH:4]=1)=O.C(O)(=O)[CH2:14][C:15]([OH:17])=[O:16].N1CCCCC1.Cl>O.N1C=CC=CC=1>[C:15]([CH:14]=[CH:1][C:3]1[S:7][C:6]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[CH:5][CH:4]=1)([OH:17])=[O:16]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 364428[2,2'-Bithiophene]-5-carboxaldehyde

생성물 1

HCID 572037503-[2,2′-Bithiophen]-5-yl-2-propenoic acid수율 62.5%

시약·촉매·용매 2

HCID 962Water용매
HCID 1049
Pyridine
용매

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온도
90 °C

실험 절차

3.88 g of 5-formyl-2,2'-bithiophene, 4.16 g of malonic acid, 15.5 ml of pyridine and 1.4 g of piperidine were heated and stirred at 90° C. in oil bath for 2 hours. Then raised the temperature to 120° C. for 10 minutes. The reaction mixture was cooled down to room temperature and diluted with 100 ml of distilled water. 40 ml of concentrated HCl was added to acidify the solution. The orange precipitate thus crystallized was further purified by silica gel chromatography. From the eluate of acetone/n-hexane (2/5), 2.95 g of product was thus obtained and the melting point thereof was 175° C. (M+ : 236). 0.16 g of pure 5-(2-dicarboxy-ethenyl)-2,2'-bithiophene was also obtained and the melting point thereof was 220°-221° C.

후처리

  1. temperatureThen raised the temperature to 120° C. for 10 minutes
  2. temperatureThe reaction mixture was cooled down to room temperature
  3. customThe orange precipitate thus crystallized
  4. customwas further purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-2f769fa9ccb34ea6871fd9b3dd1cf22c
출처 데이터셋
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05747525

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