HCID 67418524, compound → HCID 77230948, compound

HRID 1056906Notes

Reaction equation

HRID 1056906 reaction equation
[C:1]([O:4][C:5]([C:9](=[O:19])[CH2:10][C:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[CH:6]OC)(=[O:3])[CH3:2]>C1(C)C=CC=CC=1>[C:1]([O:4][C:5]1[C:9](=[O:19])[CH:10]=[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:18][CH:6]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 67418524HCID 67418524, compound

Product 1

HCID 77230948HCID 77230948, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of crude 1-methoxy-3,5-dioxo-5-phenylpent-1-en-2-yl acetate (3.5 mmol) in toluene (35 mL) was added pyridinium j-toluenesulfonate (130 mg, 0.5 mmol). The reaction mixture was heated at reflux under a nitrogen atmosphere for 1 h before being cooled and concentrated under reduced pressure and purified by flash chromatography (80 g Si02, 0-100% ethyl acetate/hexanes gradient elution) to provide 4-oxo-6-phenyl-4H-pyran-3-yl acetate. LC/MS (M+H)+ 231.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under a nitrogen atmosphere for 1 h
  3. temperaturebefore being cooled
  4. concentrationconcentrated under reduced pressure
  5. custompurified by flash chromatography (80 g Si02, 0-100% ethyl acetate/hexanes gradient elution)

Sources & evidence

ORD record
ord-9fb15b8b8dcd4ca58b0132c466e9f413
Source dataset
uspto-grants-2016_07
Patent number
US09399651B2

Reaction notes

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