Sulfuric Acid → Ethyl 5-methoxy-2,4-dioxopentanoate

HRID 872878Notes

Reaction equation

HRID 872878 reaction equation
[Na].[C:2]([O:9][CH2:10][CH3:11])(=[O:8])[C:3]([O:5]CC)=O.[CH3:12][O:13][CH2:14][C:15](=[O:17])[CH3:16].S(=O)(=O)(O)O>C(O)C>[CH3:12][O:13][CH2:14][C:15](=[O:17])[CH2:16][C:3](=[O:5])[C:2]([O:9][CH2:10][CH3:11])=[O:8]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 7268Diethyl OxalateHCID 22172MethoxyacetoneHCID 5360545Sodium

Product 1

HCID 67172400Ethyl 5-methoxy-2,4-dioxopentanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Under nitrogen atmosphere sodium (1.61 g, 70.0 mmol) was dissolved in small pieces in a flask containing dry ethanol (150 ml). Diethyl oxalate (8.15 ml, 60 mmol) and methoxyacetone (5.52 ml, 60.0 mmol) were added with a syringe. The resulting mixture was stirred at RT for 1 h. The flask was put in an ice bath and into it a mixture of sulphuric acid and ice water was added dropwise. The resulting precipitate was filtered and washed with DCM. The ethanol/DCM filtrate was evaporated. The residue was dissolved in DCM, extracted with brine and the DCM phase dried with Na2SO4, filtered and evaporated. The product was purified with flash chromatography. 1H-NMR (400 MHz; DMSO-d6): δ 1.28 (t, 3H), 3.34 (s, 3H), 4.19-4.23 (m, 2H), 4.27 (q, 2H).

Workup

  1. customThe flask was put in an ice bath and into it
  2. additionwas added dropwise
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with DCM
  5. customThe ethanol/DCM filtrate was evaporated
  6. dissolutionThe residue was dissolved in DCM
  7. extractionextracted with brine
  8. dry with materialthe DCM phase dried with Na2SO4
  9. filtrationfiltered
  10. customevaporated
  11. customThe product was purified with flash chromatography

Sources & evidence

ORD record
ord-e1f303e7ce3a4457ac08f8bac98f1314
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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