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

HRID 1289131
ノート
印刷プレビュー

反応式

HRID 1289131 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 1049
Pyridine
溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2f769fa9ccb34ea6871fd9b3dd1cf22c
出典データセット
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05747525

反応ノート

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