Water → HCID 14116086, compound

HRID 345503Notes

Reaction equation

HRID 345503 reaction equation
[H-].[Na+].[C:3]([CH2:11][C:12]#[N:13])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].O>C1(C)C=CC=CC=1>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][CH:11]([C:12]#[N:13])[C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 64799Benzoylacetonitrile

Product 1

HCID 14116086HCID 14116086, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A heptane washed suspension of 7.6 g (0.189 mole) of 60% NaH/mineral oil in 400 ml of anhydrous toluene was treated portion-wise with 25.0 g (0.172 mole) of benzoylacetonitrile under a nitrogen atmosphere. After stirring for 1 hour, 33.0 g (0.189 mole) of ethyl bromoacetate (97%) was added in one portion. The reaction was heated at reflux for 4 hours, then allowed to cool to room temperature and stirred for 20 hours. Water (500 ml) was added, and the toluene layer was extracted with water (500 ml). The toluene layer was dried over MgSO4, filtered, and the solvent evaporated under reduced pressure (42.9 g). The residual oil was fractionally distilled under vacuum to give 21.4 g (54%) of pure product.

Workup

  1. washA heptane washed
  2. temperatureThe reaction was heated
  3. temperatureat reflux for 4 hours
  4. stirringstirred for 20 hours
  5. extractionthe toluene layer was extracted with water (500 ml)
  6. dry with materialThe toluene layer was dried over MgSO4
  7. filtrationfiltered
  8. customthe solvent evaporated under reduced pressure (42.9 g)
  9. distillationThe residual oil was fractionally distilled under vacuum

Sources & evidence

ORD record
ord-6319b2181098400bbeb5d088aeceb17e
Source dataset
uspto-grants-1991_10
Patent number
US05057534

Reaction notes

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