Acetic Acid → 1,1,1-Trifluoro-8-phenyl-3,5,7-octatrien-2-one

HRID 459431Notes

Reaction equation

HRID 459431 reaction equation
[C:1]1([CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(=O)C.N1CCCCC1.[F:23][C:24]([F:29])([F:28])[C:25]([CH3:27])=[O:26]>C1COCC1>[F:23][C:24]([F:29])([F:28])[C:25](=[O:26])[CH:27]=[CH:11][CH:10]=[CH:9][CH:8]=[CH:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 9871Methyl trifluoromethyl ketoneHCID 1146512,4-Pentadienal, 5-phenyl-

Product 1

HCID 862226621,1,1-Trifluoro-8-phenyl-3,5,7-octatrien-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1,1,1-Trifluoro-8-phenyl-3,5,7-octatrien-2-one is prepared as outlined in Scheme IIIA. 1,1,1-Trifluoro-8-phenyl-3,5,7-octatrien-2-one is prepared by reacting 5-phenyl-2,4-pentadienal in THF with an equal amount of acetic acid and piperidine followed by addition of 1,1,1-trifluoroacetone at room temperature under nitrogen.

Workup

  1. custom1,1,1-Trifluoro-8-phenyl-3,5,7-octatrien-2-one is prepared

Sources & evidence

ORD record
ord-f7731148df1d40508236a4a1e9c5f0a3
Source dataset
uspto-grants-2007_03
Patent number
US07193105B2

Reaction notes

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