Water → Ethyl 2-(4-(methoxymethoxy)phenyl)propanoate

HRID 1626849Notes

Reaction equation

HRID 1626849 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=1.[H-].[Na+].I[CH3:20].O>CN(C=O)C>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:20])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 16638004Ethyl 2-(4-(methoxymethoxy)phenyl)acetate

Product 1

HCID 57742134Ethyl 2-(4-(methoxymethoxy)phenyl)propanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 2-(4-(methoxymethoxy)phenyl)acetate (1.75 g, 7.80 mmol) in DMF (50 mL) was slowly added sodium hydride (330 mg, 8.25 mmol) and iodomethane (1.13 g, 7.96 mmol) at 0° C. The reaction mixture was stirred for 1 hour at 0° C. The mixture was added water (50 mL) and extracted with EtOAc. The organic layer was dried with MgSO4. The organic layer was filtered and the filtrate was concentrated in vacuo. The residue was purified by column chromatography eluting with n-Hexane/EtOAc=15/1.

Workup

  1. customat 0° C
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried with MgSO4
  4. filtrationThe organic layer was filtered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was purified by column chromatography
  7. washeluting with n-Hexane/EtOAc=15/1

Sources & evidence

ORD record
ord-304423081fbd42f5abda5aba01194ae1
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

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