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

HRID 1357185Notes

Reaction equation

HRID 1357185 reaction equation
C([O:8][CH2:9][C:10]1[O:15][C:14](=[O:16])[C:13]([CH3:17])=[C:12]([O:18][CH2:19][O:20][CH3:21])[C:11]=1[CH3:22])C1C=CC=CC=1>CCO.[OH-].[OH-].[Pd+2]>[CH3:17][C:13]1[C:14](=[O:16])[O:15][C:10]([CH2:9][OH:8])=[C:11]([CH3:22])[C:12]=1[O:18][CH2:19][O:20][CH3:21]

Participants

4

Reactant 1

HCID 120828846-(benzyloxy)methyl-3,5-dimethyl-4-methoxymethoxy-2H-pyran-2-one

Product 1

HCID 120828853,5-dimethyl-6-hydroxymethyl-4-methoxymethoxy-2H-pyran-2-one

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

20% Pd(OH)2/C (360 mg) was added to a solution of 6-(benzyloxy)methyl-3,5-dimethyl-4-methoxymethoxy-2H-pyran-2-one (1.80 g) in EtOH (50 ml), and the mixture was vigorously stirred at room temperature for 3 hours under a hydrogen gas atmosphere. The reaction solution was celite filtered and the mother liquor was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=1/1) to obtain 3,5-dimethyl-6-hydroxymethyl-4-methoxymethoxy-2H-pyran-2-one.

Workup

  1. filtrationfiltered
  2. concentrationthe mother liquor was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=1/1)

Sources & evidence

ORD record
ord-bf1221811594424e8486d06dc7b892b2
Source dataset
uspto-grants-2003_07
Patent number
US06589984B1

Reaction notes

Loading…