Ethanol → HCID 19027723, compound

HRID 2256988Notes

Reaction equation

HRID 2256988 reaction equation
[Na].C(O)C.[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]#[N:14])=[CH:8][CH:7]=1.[C:15](OCC)(=[O:19])[CH2:16][CH2:17][CH3:18]>>[C:15]([CH:12]([C:9]1[CH:10]=[CH:11][C:6]([F:5])=[CH:7][CH:8]=1)[C:13]#[N:14])(=[O:19])[CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 4

HCID 702EthanolHCID 7762Ethyl butyrateHCID 68016Benzeneacetonitrile, 4-fluoro-HCID 5360545Sodium

Product 1

HCID 19027723HCID 19027723, compound

Procedure

10.9 g of sodium are added to 150 ml of absolute ethanol. While maintaining reflux, a solution of 49.5 g of 4-fluorophenylacetonitrile in 65.2 g of ethyl butyrate is added. The reaction mixture is refluxed for 4 hours and then left to stand overnight at room temperature. The solvents are concentrated under vacuum and the residue is taken up in water and washed with ether. The aqueous phase is cooled in an ice bath and acidified to pH 5-6 by the addition of concentrated acetic acid to give crystals, which are filtered off, washed with water and dissolved in methylene chloride.

Workup

  1. temperatureWhile maintaining
  2. temperaturereflux
  3. temperatureThe reaction mixture is refluxed for 4 hours
  4. waitleft
  5. concentrationThe solvents are concentrated under vacuum
  6. washwashed with ether
  7. temperatureThe aqueous phase is cooled in an ice bath
  8. additionacidified to pH 5-6 by the addition of concentrated acetic acid
  9. customto give crystals, which
  10. filtrationare filtered off
  11. washwashed with water
  12. dissolutiondissolved in methylene chloride

Sources & evidence

ORD record
ord-f69d480101f64749b5c5c58442d6c1e1
Source dataset
uspto-grants-1997_08
Patent number
US05656631

Reaction notes

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