Acetic Acid → HCID 67343678, compound

HRID 1669768Notes

Reaction equation

HRID 1669768 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[CH:13]=O.[F:15][C:16]([F:29])([F:28])[C:17](=[O:27])[CH2:18][C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:20].C(O)(=O)C.N1CCCCC1>ClCCl>[F:15][C:16]([F:28])([F:29])[C:17](=[O:27])[C:18](=[CH:13][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[O:3][C:2]([CH3:1])=[CH:11][C:10]2=[O:12])[C:19]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[O:20]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 675894,4,4-Trifluoro-1-phenyl-1,3-butanedioneHCID 133748832-Methyl-4-oxo-4H-chromene-8-carbaldehyde

Product 1

HCID 67343678HCID 67343678, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 200 mg (1.06 mmol) of 2-methyl-4-oxo-4H-chromene-8-carbaldehyde in 20 ml of dichloromethane is mixed with 229.73 mg (1.06 mmol) of 4,4,4-trifluoro-1-phenyl-1,3-butanedione, 0.08 ml (1.33 mmol) of acetic acid and 0.01 ml (0.11 mmol) of piperidine and stirred under reflux with a water trap overnight. After cooling, the mixture is diluted with dichloromethane and washed with saturated sodium chloride solution. The organic phase is dried over sodium sulfate and concentrated. 474 mg (>100% of theory) of the desired product are obtained as a yellow oil which is reacted further without purification.

Workup

  1. temperatureunder reflux with a water trap overnight
  2. temperatureAfter cooling
  3. washwashed with saturated sodium chloride solution
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a9207a26c3f34a1d8bb01a6cfd7bbd71
Source dataset
uspto-grants-2011_08
Patent number
US07989633B2

Reaction notes

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