Methyl 4-methoxyacetoacetate → HCID 136035589, compound

HRID 1674418Notes

Reaction equation

HRID 1674418 reaction equation
[CH3:1][O:2][CH2:3][C:4](=O)[CH2:5][C:6]([O:8]C)=O.Cl.[C:12](=[NH:17])([NH2:16])[CH2:13][CH2:14][CH3:15].C[O-].[Na+]>CO.C(OCC)(=O)C>[CH3:1][O:2][CH2:3][C:4]1[N:16]=[C:12]([CH2:13][CH2:14][CH3:15])[NH:17][C:6](=[O:8])[CH:5]=1

Participants

6

Reactant 3

HCID 123500Methyl 4-methoxyacetoacetateHCID 10942334Sodium MethoxideHCID 12828983Butanimidamide hydrochloride

Product 1

HCID 136035589HCID 136035589, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 4-methoxy-3-oxobutanoate (15.0 g), butanimidamide hydrochloride (15 g) and sodium methoxide (28% in methanol, 51 mL) in methanol (150 mL) was stirred overnight. The reaction mixture was diluted with ethyl acetate, washed with 1M hydrochloric acid, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a pale yellow oil (17 g, 91%).

Workup

  1. washwashed with 1M hydrochloric acid
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-e432a2d761374147b52699a8fbb54b17
Source dataset
uspto-grants-2011_08
Patent number
US07998968B2

Reaction notes

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