Sodium Bromide → 6-bromomethyl-3,5-dimethyl-4-methoxymethoxy-2H-pyran-2-one

HRID 1357187Notes

Reaction equation

HRID 1357187 reaction equation
[Br-:1].[Na+].[CH3:3][C:4]1[C:5](=[O:21])[O:6][C:7]([CH2:15]OS(C)(=O)=O)=[C:8]([CH3:14])[C:9]=1[O:10][CH2:11][O:12][CH3:13]>CN(C=O)C>[Br:1][CH2:15][C:7]1[O:6][C:5](=[O:21])[C:4]([CH3:3])=[C:9]([O:10][CH2:11][O:12][CH3:13])[C:8]=1[CH3:14]

Participants

4

Reactant 2

HCID 253881Sodium BromideHCID 120829703,5-dimethyl-4-methoxymethoxy-6-(methylsulfonyloxy)methyl-2H-pyran-2-one

Product 1

HCID 120829716-bromomethyl-3,5-dimethyl-4-methoxymethoxy-2H-pyran-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium bromide (500 mg) was added to a solution of 3,5-dimethyl-4-methoxymethoxy-6-(methylsulfonyloxy)methyl-2H-pyran-2-one (1.35 g) in DMF (20 ml), and after the stirring the mixture at room temperature for one hour, the reaction solution 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=1/1) to obtain 6-bromomethyl-3,5-dimethyl-4-methoxymethoxy-2H-pyran-2-one.

Workup

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

Sources & evidence

ORD record
ord-cf7f029ff12b4c058965df3a2b7b11e3
Source dataset
uspto-grants-2003_07
Patent number
US06589984B1

Reaction notes

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