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

HRID 1357186Notes

Reaction equation

HRID 1357186 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1[C:10](=[O:22])[O:11][C:12]([CH2:20][OH:21])=[C:13]([CH3:19])[C:14]=1[O:15][CH2:16][O:17][CH3:18].[CH3:23][S:24](Cl)(=[O:26])=[O:25].O>C1COCC1.CCOC(C)=O>[CH3:8][C:9]1[C:10](=[O:22])[O:11][C:12]([CH2:20][O:21][S:24]([CH3:23])(=[O:26])=[O:25])=[C:13]([CH3:19])[C:14]=1[O:15][CH2:16][O:17][CH3:18]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 120828853,5-dimethyl-6-hydroxymethyl-4-methoxymethoxy-2H-pyran-2-one

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (606 mg) was added to a solution of 3,5-dimethyl-6-hydroxymethyl-4-methoxymethoxy-2H-pyran-2-one (1.26 g) in THF (50 ml), and after stirring the mixture at room temperature for one hour, methanesulfonyl chloride (1.05 g) was added and the mixture was stirred at room temperature overnight. Water was added to the reaction solution, 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 3,5-dimethyl-4-methoxymethoxy-6-(methylsulfonyloxy) methyl-2H-pyran-2-one.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. dry with materialthe organic layer was dried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=1/1)

Sources & evidence

ORD record
ord-019a08c516ae426db538ececa5acd8f7
Source dataset
uspto-grants-2003_07
Patent number
US06589984B1

Reaction notes

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