Ethyl cyanoacetate → HCID 22634765, compound

HRID 2417366Notes

Reaction equation

HRID 2417366 reaction equation
[C:1]([C:5]1[C:6](=[O:15])[O:7][C:8]2[C:9]=1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)(=O)[CH2:2][CH3:3].C(CC(OCC)=O)#[N:17].[O-][CH2:25][CH3:26].[Na+].[Na]>C(O)C>[C:3]([C:2]1[C:10]2[C:9]([CH:8]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:5]([C:6]([OH:7])=[O:15])[C:1]=1[CH2:25][CH3:26])#[N:17]

Participants

6

Reactant 4

HCID 7764Ethyl cyanoacetateHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 22634769HCID 22634769, compound

Product 1

HCID 22634765HCID 22634765, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

3.62 g (17.9 mmol) of 3-propionylcycloheptafuran-2-one and 3.8 ml (35.8 mmol) of ethyl cyanoacetate were dissolved in 50 ml of ethanol. The solution was mixed with a solution of sodium ethoxide prepared from 80 ml of ethanol and 1.65 g (71.7 mmol) of sodium, at 0° C. After the mixed solution was stirred overnight at room temperature, the obtained reaction solution was concentrated up to two times an initial concentration thereof. The concentrated solution was diluted with 200 ml of water and extracted with dichloromethane. Thereafter, an aqueous phase of the extract was mixed with dilute hydrochloric acid to acidify the aqueous phase, thereby obtaining a crystallized product. After filtration, the crystallized product was dried under a reduced pressure to obtain 3.73 g of 1-cyano-2-ethylazulene-3-carboxylic acid (yield: 93%).

Workup

  1. customthe obtained reaction solution
  2. concentrationwas concentrated up to two times an initial
  3. concentrationconcentration
  4. additionThe concentrated solution was diluted with 200 ml of water
  5. extractionextracted with dichloromethane
  6. additionThereafter, an aqueous phase of the extract was mixed with dilute hydrochloric acid
  7. customobtaining a crystallized product
  8. filtrationAfter filtration
  9. customthe crystallized product was dried under a reduced pressure

Sources & evidence

ORD record
ord-cf541f57800948be8b6e5474651b490a
Source dataset
uspto-grants-2004_11
Patent number
US06825371B2

Reaction notes

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