Acetic Acid → 3-(2,3,6-Trifluorophenyl)but-3-en-2-one

HRID 706379Notes

Reaction equation

HRID 706379 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[CH2:10][C:11](=[O:13])[CH3:12].[C:14](O)(=O)C.N1CCCCC1.C=O>CC#N>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[C:10](=[CH2:14])[C:11](=[O:13])[CH3:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 8082PiperidineHCID 552746091-(2,3,6-Trifluorophenyl)propan-2-one

Product 1

HCID 898150313-(2,3,6-Trifluorophenyl)but-3-en-2-oneYield 205%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 18 (3.5 g, 18.6 mmol), acetic acid (0.34 ml, 5.58 mmol), piperidine (0.37 ml, 3.72 mmol), formaldehyde (6.0 g, 37% aqueous solution) in MeCN (20 mL) was heated over weekend. The conversion was about 60%. Reaction was heated to 70° C. overnight. The mixture was concentrated and extracted with MTBE and HCl (0.5N). The organic layer was washed with aqueous K2CO3 (0.5N) and water, in turns. The organic layer was concentrated. The product was isolated by chromatography column (hexane and EtOAc), yielding 31 (2.29 g, 61.5%).

Workup

  1. customReaction
  2. concentrationThe mixture was concentrated
  3. extractionextracted with MTBE and HCl (0.5N)
  4. washThe organic layer was washed with aqueous K2CO3 (0.5N) and water, in turns
  5. concentrationThe organic layer was concentrated
  6. customThe product was isolated by chromatography column (hexane and EtOAc)

Sources & evidence

ORD record
ord-f5207df9259a43d1a355e67e473d0a50
Source dataset
uspto-grants-2015_11
Patent number
US09174989B2

Reaction notes

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