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

HRID 1357184Notes

Reaction equation

HRID 1357184 reaction equation
C(N(C(C)C)CC)(C)C.[CH2:10]([O:17][CH2:18][C:19]1[O:24][C:23](=[O:25])[C:22]([CH3:26])=[C:21]([OH:27])[C:20]=1[CH3:28])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH3:29][O:30][CH2:31]Cl>C1COCC1>[CH2:10]([O:17][CH2:18][C:19]1[O:24][C:23](=[O:25])[C:22]([CH3:26])=[C:21]([O:27][CH2:29][O:30][CH3:31])[C:20]=1[CH3:28])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 547300356-(benzyloxy)methyl-3,5-dimethyl-4-hydroxy-2H-pyran-2-one

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisopropylethylamine (2.1 ml) was added to a solution of 6-(benzyloxy)methyl-3,5-dimethyl-4-hydroxy-2H-pyran-2-one (2.60 g) in THF (50 ml), and after stirring the mixture at room temperature for one hour, chloromethyl methyl ether (921 μl) was added at 0° C. and the mixture was stirred at room temperature for one hour. After concentrating the reaction solution 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-methoxymethoxy-2H-pyran-2-one.

Workup

  1. stirringthe mixture was stirred at room temperature for one hour
  2. concentrationAfter concentrating the reaction solution under reduced pressure, water
  3. additionwas 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-3f9b704b5b0f457ea821a6500a87f3f9
Source dataset
uspto-grants-2003_07
Patent number
US06589984B1

Reaction notes

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