Hydrochloric Acid → 4-acetyloxy-6-(benzyloxy)methyl-3,5-dimethyl-2H-pyran-2-one

HRID 1357182Notes

Reaction equation

HRID 1357182 reaction equation
O[Li].O.[CH2:4]([O:11][CH2:12][C:13](=[O:24])[CH:14]([CH3:23])[C:15](=[O:22])[CH:16]([CH3:21])[C:17]([O:19]C)=O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Cl.C1C[O:29][CH2:28][CH2:27]1>>[C:28]([O:22][C:15]1[C:14]([CH3:23])=[C:13]([CH2:12][O:11][CH2:4][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:24][C:17](=[O:19])[C:16]=1[CH3:21])(=[O:29])[CH3:27]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 12082881Methyl 6-benzyloxy-2,4-dimethyl-3,5-dioxohexanoate

Product 1

HCID 120828824-acetyloxy-6-(benzyloxy)methyl-3,5-dimethyl-2H-pyran-2-one

Procedure

An aqueous solution (6 ml) of LiOH-hydrate (64 mg) was added to a solution of methyl 6-benzyloxy-2,4-dimethyl-3,5-dioxohexanoate (430 mg) in THF (10 ml), and the mixture was stirred at room temperature for 1.5 hours. The reaction solution was neutralized with diluted hydrochloric acid, and after distilling off the volatile components under reduced pressure, extraction was performed with AcOEt at pH 3. The organic layer was dried with MgSO4 and then filtered and concentrated. Ac2O (6 ml) was added to the residue, and after stirring at room temperature for 30 minutes, pyridine (4 ml) was added and the mixture was stirred at room temperature for one hour. The reaction solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/AcOEt=3/1→12/5) to obtain 4-acetyloxy-6-(benzyloxy)methyl-3,5-dimethyl-2H-pyran-2-one.

Workup

  1. distillationafter distilling off the volatile components
  2. extractionunder reduced pressure, extraction
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. additionAc2O (6 ml) was added to the residue
  7. stirringafter stirring at room temperature for 30 minutes
  8. additionpyridine (4 ml) was added
  9. stirringthe mixture was stirred at room temperature for one hour
  10. concentrationThe reaction solution was concentrated under reduced pressure
  11. customthe residue was purified by silica gel column chromatography (n-hexane/AcOEt=3/1→12/5)

Sources & evidence

ORD record
ord-73518805d6fa40d2bd124df88032c3f1
Source dataset
uspto-grants-2003_07
Patent number
US06589984B1

Reaction notes

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