Methyl iodide → Ethyl 3-(2-cyanopropan-2-yl)benzoate

HRID 564012Notes

Reaction equation

HRID 564012 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([C:13]#[N:14])[CH3:12])[CH:6]=1)[CH3:2].[H-].[Na+].[CH3:18]I>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([C:13]#[N:14])([CH3:18])[CH3:12])[CH:6]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67007698Ethyl 3-(1-cyanoethyl)benzoate

Product 1

HCID 67008001Ethyl 3-(2-cyanopropan-2-yl)benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(1-Cyano-ethyl)-benzoic acid ethyl ester were dissolved in 4 ml dry DMF. Under nitrogen atmosphere, 138 mg of 60% sodium hydride and 423 mg methyl iodide were added at RT. The mixture was stirred for 16 hrs, then quenched by addition of 1 ml methanol and evaporated. The residue was purified by chromatography on silica in ethyl acetate/heptane mixtures.

Workup

  1. customquenched by addition of 1 ml methanol
  2. customevaporated
  3. customThe residue was purified by chromatography on silica in ethyl acetate/heptane mixtures

Sources & evidence

ORD record
ord-9eac2464aca445b09a7c7c939b5548e1
Source dataset
uspto-grants-2011_11
Patent number
US08067599B2

Reaction notes

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