Ethanol → Diethyl 2-cyano-3-(p-fluorophenyl)glutarate

HRID 1531351Notes

Reaction equation

HRID 1531351 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[H-].[Na+].[F:11][C:12]1[CH:30]=[CH:29][C:15]([CH:16]=[C:17](C2C=CC=CC=2)[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14][CH:13]=1.C(O)C>CN(C)C=O.O>[C:1]([CH:3]([CH:16]([C:15]1[CH:14]=[CH:13][C:12]([F:11])=[CH:30][CH:29]=1)[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2]

Participants

7

Reactant 4

HCID 702EthanolHCID 7764Ethyl cyanoacetateHCID 24758Sodium hydrideHCID 70033408Ethyl p-fluorophenylcinnamate

Product 1

HCID 10935698Diethyl 2-cyano-3-(p-fluorophenyl)glutarateYield 105.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To 1 g of ethyl cyanoacetate dissolved in 5 mL of N,N-dimethylformamide, 0.5 g of sodium hydride was added under cooling with ice, and after stirring at room temperature for 30 minutes, 1.5 g of ethyl p-fluorophenylcinnamate was added. The reaction mixture was stirred at room temperature for 4 hours. After addition of ethanol under cooling with ice, the reaction mixture was poured into iced water and extracted with a solvent mixture of hexane and ethyl acetate. The extract was washed with water, and dried and concentrated. The resulting oily substance was separated by silica gel column chromatography (hexane:ethyl acetate=9:1) to obtain 1.8 g of diethyl 2-cyano-3-(p-fluorophenyl)glutarate as a diastereomer mixture.

Workup

  1. temperatureunder cooling with ice
  2. stirringThe reaction mixture was stirred at room temperature for 4 hours
  3. temperatureunder cooling with ice
  4. extractionextracted with a solvent mixture of hexane and ethyl acetate
  5. washThe extract was washed with water
  6. customdried
  7. concentrationconcentrated
  8. customThe resulting oily substance was separated by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-04dae7e3f65b46308257cd436e9f7226
Source dataset
uspto-grants-2001_03
Patent number
US06197960B1

Reaction notes

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