Hydrochloric Acid → (E)-3-(5-(4-chloro-3-(trifluoromethyl)phenyl)furan-2-yl)acrylic acid

HRID 872534ノート

反応式

HRID 872534 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([CH:13]=O)=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:15]([F:18])([F:17])[F:16].N1CCCCC1.C(O)(=O)[CH2:26][C:27]([OH:29])=[O:28].Cl>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11](/[CH:13]=[CH:26]/[C:27]([OH:29])=[O:28])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:15]([F:16])([F:17])[F:18]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 8082PiperidineHCID 7994205-[4-Chloro-3-(trifluoromethyl)phenyl]furan-2-carbaldehyde

生成物 1

HCID 67169287(E)-3-(5-(4-chloro-3-(trifluoromethyl)phenyl)furan-2-yl)acrylic acid収率 500.2%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

5-(4-chloro-3-(trifluoromethyl)phenyl)furan-2-carbaldehyde (3.32 g, 13.4 mmol) was dissolved in pyridine (16.6 ml) and piperidine (0.66 ml) was added. Malonic acid (1.67 g, 1.61 mmol) was added and the reaction mixture was refluxed for 4 h. Cooled reaction mixture was poured into a solution of ice (100 ml) water (100 ml) and conc. HCl (100 ml). The precipitate was filtered and washed with cold water and recrystallised from ethanol to afford 2.55 g of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 6.44 (d, 1H), 7.08 (d, 1H), 7.40 (m, 1H), 7.43 (d, 1H), 7.81 (d, 1H), 8.14 (m, 1H), 8.21 (m, 1H), 12.44 (m, 1H).

後処理

  1. temperaturethe reaction mixture was refluxed for 4 h
  2. temperatureCooled
  3. customreaction mixture
  4. filtrationThe precipitate was filtered
  5. washwashed with cold water
  6. customrecrystallised from ethanol

出典と根拠

ORDレコード
ord-0cf334a8a36349bb81296a2b7755e990
出典データセット
uspto-grants-2015_03
特許番号
US08975254B2

反応ノート

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