Methyl iodide → Ethyl 2-(4-cyanophenyl)propanoate

HRID 1428791Notes

Reaction equation

HRID 1428791 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1)#[N:2].[H-].[Na+].I[CH3:18]>CN(C)C=O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:18])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 279718Ethyl 2-(4-cyanophenyl)acetate

Product 1

HCID 4550989Ethyl 2-(4-cyanophenyl)propanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of ethyl 2-(4-cyanophenyl)acetate (0.8 g, 4.101 mmol) in anhydrous dimethylformamide were added 60% sodium hydride (180 mg, 4.511 mol) and Iodo methane were added after 10 min with an ice bath. The reaction mixture was stirred for 1 h hours, quenched with water and extracted with ethylacetate which is washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filterate was concentrated under reduced pressure. The residue was purified by column chromatography. Ethyl 2-(4-cyanophenyl)propanoate (453 mg) was obtained as 48%

Workup

  1. additionwere added after 10 min with an ice bath
  2. customquenched with water
  3. extractionextracted with ethylacetate which
  4. washis washed with water and brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filterate was concentrated under reduced pressure
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-88c7ec33da1e4598bf5467e84d558503
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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