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

HRID 872534Notes

Reaction equation

HRID 872534 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-0cf334a8a36349bb81296a2b7755e990
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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