Trifluoroacetic acid → 4H-Pyran-4-one, 5-hydroxy-2-methyl-

HRID 1461240Notes

Reaction equation

HRID 1461240 reaction equation
COC1C=CC(C[O:8][C:9]2[C:10](=[O:16])[CH:11]=[C:12]([CH3:15])[O:13][CH:14]=2)=CC=1.FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1>[OH:8][C:9]1[C:10](=[O:16])[CH:11]=[C:12]([CH3:15])[O:13][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19980216HCID 19980216, compound

Product 1

HCID 695214H-Pyran-4-one, 5-hydroxy-2-methyl-

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

5-p-Methoxybenzyloxy-2-methyl-4-pyrone, 10 g, was dissolved in 10 ml of anisole and 15 ml of trifluoroacetic acid was dropwise added to the solution under ice cooling. After stirring at the same temperature for 3 hours, the mixture was concentrated under reduced pressure. The concentrate was separated and purified by flash column chromatography (eluting solution; chloroform: methanol=20:1) using Wako Gel C-300 (200 g) to give 2.4 g of the title compound.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customThe concentrate was separated
  3. custompurified by flash column chromatography (eluting solution; chloroform: methanol=20:1)

Sources & evidence

ORD record
ord-09fbf1e2c11d480cab7a6727bd463848
Source dataset
uspto-grants-1991_12
Patent number
US05075299

Reaction notes

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