Sodium hydride → HCID 57843543, compound

HRID 734277Notes

Reaction equation

HRID 734277 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([Cl:13])[CH:7]=1)[CH3:5].[CH3:15][O:16][CH:17]([O:20][CH3:21])[CH2:18]Br.[H-].[Na+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:14])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([Cl:13])[CH:7]=1)([CH3:5])[CH2:18][CH:17]([O:20][CH3:21])[O:16][CH3:15]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 816722-Bromo-1,1-dimethoxyethaneHCID 11402033HCID 11402033, compound

Product 1

HCID 57843543HCID 57843543, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 35 g (150 mmol) 2-(3,4-dichloro-phenyl)-propionic acid methyl ester (Journal of Medicinal Chemistry (2004), 47(23), 5753-5765), 31.7 g (188 mmol) bromoacetaldehyde dimethyl acetal (commercially available and 6.6 g (165 mmol) NaH (55%) in 100 mL DMF was stirred at room temperature and afterwards evaporated to dryness. Ice water and ethyl acetate was added and the organic fraction was washed with sat. NaCl aq., dried with Na2SO4 and evaporated. The residue was purified by column chromatography on silica eluting with a mixture of ethyl acetate and hexane. The product containing fractions were evaporated to yield 29.6 g (61%) of the title compound as yellow liquid.

Workup

  1. customafterwards evaporated to dryness
  2. additionIce water and ethyl acetate was added
  3. washthe organic fraction was washed with sat. NaCl aq.
  4. dry with materialdried with Na2SO4
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica eluting with a mixture of ethyl acetate and hexane
  7. additionThe product containing fractions
  8. customwere evaporated

Sources & evidence

ORD record
ord-78a6691dd05743b6920d122258184780
Source dataset
uspto-grants-2009_09
Patent number
US07592345B2

Reaction notes

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