Dimethylformamide → HCID 86679386, compound

HRID 1428804Notes

Reaction equation

HRID 1428804 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][C:3]=1[CH3:15].[CH3:16][N:17](C)C=O>[C-]#N.[Zn+2].[C-]#N.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:16]([C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][C:3]=1[CH3:15])#[N:17]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 86679385HCID 86679385, compound

Product 1

HCID 86679386HCID 86679386, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

To a stirred solution of ethyl 2-(4-iodo-3-methylphenyl)propanoate (1.22 g, 5.34 mmol) in anhydrous dimethylformamide were added zinc cyanide (645 mg, 5.50 mmol) and tetrakis(triphenylphosphine) palladium (617 mg, 0.53 mmol). The reaction mixture was refluxed for overnight then cooled to room temperature. The mixture was filtered using celite pad and the filtrate was evaporated. The residue was diluted with ethylacetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to get the crude. The crude was purified by column chromatography. Ethyl 2-(4-cyano-3-methylphenyl)propanoate (1.05 g) was obtained as 90% yield.

Workup

  1. temperatureThe reaction mixture was refluxed for overnight
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated
  4. additionThe residue was diluted with ethylacetate
  5. washwashed with water and brine
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customto get the crude
  10. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-09d76701a95f4d199eaec87a8dab7081
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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