Diethyl 2-(ethoxymethylidene)-3-oxobutanedioate → HCID 19800636, compound

HRID 1646447Notes

Reaction equation

HRID 1646447 reaction equation
[N+:1]([CH2:4][C:5](=[O:7])[CH3:6])([O-:3])=[O:2].C(O[CH:11]=[C:12]([C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14])C.C([O-])(=O)C.[Na+]>C(O)C>[OH:7][C:5]1[CH:6]=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:12](=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2])[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 40590Diethyl 2-(ethoxymethylidene)-3-oxobutanedioateHCID 662962-Propanone, 1-nitro-HCID 517045Sodium Acetate

Product 1

HCID 19800636HCID 19800636, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of nitro-2-propanone (63.50 g, 0.616 mol), (ethoxymethylene)oxalacetic acid, diethyl ester (151.1 g, 0.616 mol) and ethanol at 5° C. under a nitrogen atmosphere is treated with sodium acetate (101.1 g, 1.23 mol), stirred overnight at room temperature, and concentrated in vacuo. The resultant residue is chromatographed (silica gel, 1% ethyl acetate:hexanes eluent). The chromatographed material is taken up in ethyl acetate and extracted with an equivalent of aqueous sodium hydroxide. The basic layer is acidified to pH 2-3 with concentrated hydrochloric acid and extracted with ethyl acetate. The organic extract is dried and concentrated in vacuo to give the title product as a yellow oil, 16.0 g, identified by NMR and mass spectral analyses.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resultant residue is chromatographed (silica gel, 1% ethyl acetate:hexanes eluent)
  3. extractionextracted with an equivalent of aqueous sodium hydroxide
  4. extractionextracted with ethyl acetate
  5. extractionThe organic extract
  6. customis dried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e70d99adb1ff481d8a82945502db8c9f
Source dataset
uspto-grants-1993_01
Patent number
US05180419

Reaction notes

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