Methyl 4-methoxyacetoacetate → HCID 178494553, compound

HRID 1241399Notes

Reaction equation

HRID 1241399 reaction equation
[CH3:1][O:2][CH2:3][C:4](=O)[CH2:5][C:6]([O:8]C)=O.C(O)(=O)C.[CH:15]([NH2:17])=[NH:16].C[O-].[Na+]>CO>[CH3:1][O:2][CH2:3][C:4]1[N:17]=[CH:15][N:16]=[C:6]([OH:8])[CH:5]=1

Participants

5

Reactant 3

HCID 123500Methyl 4-methoxyacetoacetateHCID 160693Formamidine acetateHCID 10942334Sodium Methoxide

Product 1

HCID 178494553HCID 178494553, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of methyl 4-methoxyacetoacetate (2.0 g, 13.69 mmole) in MeOH (15 mL) was added formamidine acetate (1.57 g, 15.05 mmole) and NaOMe (6.5 mL of a 25% by weight solution in MeOH, 30.11 mmole) then the mixture was heated to reflux. After 18 hours, the mixture was cooled to room temperature and concentrated to dryness. The residue was taken up in H2O and the pH adjusted to 7. The aqueous mixture was extracted with CHCl3 (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated to give the title compound which was sufficiently pure for use in the next step without purification. 1H-NMR (500 MHz, CDCl3) δ 8.17 (s, 1H), 6.60 (s, 1H), 4.38 (s, 2H), 3.50 (s, 3H).

Workup

  1. temperature30.11 mmole) then the mixture was heated to reflux
  2. concentrationconcentrated to dryness
  3. extractionThe aqueous mixture was extracted with CHCl3 (3×)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8bd1d86402be4811891f26ad7443b95d
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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