Diethyl 2-(ethoxymethylidene)-3-oxobutanedioate → Diethyl 5-ethylpyridine-2,3-dicarboxylate

HRID 1734438Notes

Reaction equation

HRID 1734438 reaction equation
C(O[CH:4]=[C:5]([C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.O1CC[N:21]([CH:24]=[CH:25][CH2:26][CH3:27])CC1>>[CH2:26]([C:25]1[CH:4]=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:21][CH:24]=1)[CH3:27]

Participants

3

Reactant 2

HCID 40590Diethyl 2-(ethoxymethylidene)-3-oxobutanedioateHCID 5809771-Morpholinobutene

Product 1

HCID 10857926Diethyl 5-ethylpyridine-2,3-dicarboxylateYield 57%

Procedure

Diethyl ethoxymethyleneoxalacetate (3.17 g, 0.013 mol) is added to a solution of 1-morpholinobutene (1.84 g, 0,013 mol) dissolved in CH2C12 (40 mL) at 0°. The solution is concentrated in vacuo, and ammonium acetate (50 g), ammonium hydroxide (10 mL), tetrahydrofuran (20 mL) and 95% ethanol (20 mL) are added. The solution is heated to reflux for 30 minutes, then held at 3° for 72 hours. The reaction solution is then partitioned between water and ethyl acetate. The organic layer is dried over sodium sulfate and concentrated in vacuo to give the product (1.85 g, 0.0074 mol, 57%).

Workup

  1. dissolutiondissolved in CH2C12 (40 mL) at 0°
  2. concentrationThe solution is concentrated in vacuo, and ammonium acetate (50 g), ammonium hydroxide (10 mL), tetrahydrofuran (20 mL) and 95% ethanol (20 mL)
  3. additionare added
  4. temperatureThe solution is heated
  5. temperatureto reflux for 30 minutes
  6. customThe reaction solution is then partitioned between water and ethyl acetate
  7. dry with materialThe organic layer is dried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f016665e6e2e4911b2018ce131930590
Source dataset
uspto-grants-1996_07
Patent number
US05534484

Reaction notes

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