Sodium hydride → HCID 59570909, compound

HRID 2192927Notes

Reaction equation

HRID 2192927 reaction equation
[H-].[Na+].[OH:3][C:4]([CH3:10])([CH3:9])[C:5]([O:7][CH3:8])=[O:6].[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19]Cl)=[CH:15][CH:14]=1.[Cl-].[NH4+]>CN(C=O)C>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][O:3][C:4]([CH3:10])([CH3:9])[C:5]([O:7][CH3:8])=[O:6])=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 699934-Methyloxybenzyl chlorideHCID 75024Methyl alpha-hydroxyisobutyrate

Product 1

HCID 59570909HCID 59570909, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 60% sodium hydride (2.30 g) and DMF (60.2 mL) was slowly added methyl 2-hydroxy-2-methylpropanoate (6.02 mL) under ice-cooling. Further, 4-(chloromethyl)phenyl methyl ether (7.83 mL) was added thereto, followed by stirring at room temperature for 2 hours. To the reaction mixture was added saturated aqueous ammonium chloride solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (chloroform:hexane=20:80) to obtain methyl 2-[(4-methoxybenzyl)oxy]-2-methylpropanoate (12.5 g) as a colorless oily substance.

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customthe obtained residue was purified by silica gel column chromatography (chloroform:hexane=20:80)

Sources & evidence

ORD record
ord-4c43c0f91dc547c580637ef2b6f206b4
Source dataset
uspto-grants-2012_12
Patent number
US08329707B2

Reaction notes

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