Phenylacetonitrile → HCID 12764929, compound

HRID 569749Notes

Reaction equation

HRID 569749 reaction equation
[H-].[Na+].[C:3]1([CH2:9][C:10]#[N:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>CN(C)C=O.C(OCC)(=O)C.O>[C:10]([CH:9]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])#[N:11]

Participants

7

Reactant 3

HCID 8794PhenylacetonitrileHCID 24758Sodium hydrideHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 12764929HCID 12764929, compoundYield 58.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5 g of sodium hydride (as a 55% w/w dispersion in mineral oil) were added slowly to a solution of 11.7 g of phenylacetonitrile and 19.5 g of ethyl 4-bromobutyrate in 150 ml of dimethylformamide, and the reaction mixture was stirred for 4 hours at room temperature. It was then dissolved in ethyl acetate and water. The ethyl acetate layer was separated, washed with an aqueous solution of potassium bisulfate and then with an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The oily residue was subjected to silica gel column chromatography using a 1:4 by volume mixture of ethyl acetate and cyclohexane as eluent, to give 13.5 g of the title compound as a colorless liquid.

Workup

  1. customThe ethyl acetate layer was separated
  2. washwashed with an aqueous solution of potassium bisulfate
  3. dry with materialwith an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated by evaporation under reduced pressure
  5. additionby volume mixture of ethyl acetate and cyclohexane as eluent

Sources & evidence

ORD record
ord-250e6b549fb2498e9874aeb5af131ee3
Source dataset
uspto-grants-1988_03
Patent number
US04734410

Reaction notes

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