Hydrochloric Acid → Dimethyl 2-cyano-3-phenylpentanedioate

HRID 1691660Notes

Reaction equation

HRID 1691660 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[N:2].[H-].[Na+].[C:10]([O:20][CH3:21])(=[O:19])[CH:11]=[CH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>C1(C)C=CC=CC=1.CO>[C:1]([CH:3]([CH:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:11][C:10]([O:20][CH3:21])=[O:19])[C:4]([O:6][CH3:7])=[O:5])#[N:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 76442-Propenoic acid, 3-phenyl-, methyl esterHCID 7747Methyl cyanoacetateHCID 24758Sodium hydride

Product 1

HCID 59178512Dimethyl 2-cyano-3-phenylpentanedioate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a mixed solution of 5 g of methyl cyanoacetate, 20 mL of methanol, and 20 mL of toluene was added 1.61 g of sodium hydride (55% oil-dispersion) under ice-cooling. After stirring at room temperature for 30 minutes, to the reaction mixture was added 3.24 mL of methyl cinnamate, followed by stirring at 66° C. for 15 hours. The reaction mixture was cooled to room temperature, and 1 M hydrochloric acid was then added thereto to adjust the pH of the solution to about 7. After extraction with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain 5.19 g of dimethyl 2-cyano-3-phenylpentanedioate.

Workup

  1. temperaturecooling
  2. stirringby stirring at 66° C. for 15 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. extractionAfter extraction with ethyl acetate
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-eee917e9a5de4a9e96854f28095461bc
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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