Water → 6-(benzyloxy)methyl-3,5-dimethyl-4-hydroxy-2H-pyran-2-one

HRID 1357183Notes

Reaction equation

HRID 1357183 reaction equation
C([O-])([O-])=O.[K+].[K+].O.C([O:11][C:12]1[C:17]([CH3:18])=[C:16]([CH2:19][O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[O:15][C:14](=[O:28])[C:13]=1[CH3:29])(=O)C>CO>[CH2:21]([O:20][CH2:19][C:16]1[O:15][C:14](=[O:28])[C:13]([CH3:29])=[C:12]([OH:11])[C:17]=1[CH3:18])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 120828824-acetyloxy-6-(benzyloxy)methyl-3,5-dimethyl-2H-pyran-2-one

Product 1

HCID 547300356-(benzyloxy)methyl-3,5-dimethyl-4-hydroxy-2H-pyran-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

K2CO3 (3.0 g) and water (10 ml) were added to a solution of 4-acetyloxy-6-(benzyloxy)methyl-3,5-dimethyl-2H-pyran-2-one (6.08 g) in MeOH (100 ml), and after stirring at room temperature overnight, the reaction solution was celite filtered and the mother liquor was concentrated under reduced pressure. Water was added to the residue, extraction was performed with AcOEt, and the organic layer was dried with Na2SO4 and then filtered and concentrated. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=5/1→1/1) to obtain 6-(benzyloxy)methyl-3,5-dimethyl-4-hydroxy-2H-pyran-2-one.

Workup

  1. filtrationfiltered
  2. concentrationthe mother liquor was concentrated under reduced pressure
  3. additionWater was added to the residue, extraction
  4. dry with materialthe organic layer was dried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=5/1→1/1)

Sources & evidence

ORD record
ord-1e935a72f2ae4589abb03d571cf8fbf2
Source dataset
uspto-grants-2003_07
Patent number
US06589984B1

Reaction notes

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