Methyl iodide → Ethyl 2-(4-nitrophenyl)propionate

HRID 1626889Notes

Reaction equation

HRID 1626889 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)[CH3:2].[H-].[Na+].I[CH3:19]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:15])[CH:5]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)[CH3:19])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 79517Ethyl 4-nitrophenylacetate

Product 1

HCID 3016550Ethyl 2-(4-nitrophenyl)propionate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (4-Nitro-phenyl)-acetic acid ethyl ester (3.88 g) in DMF (15 mL) was slowly added sodium hydride (0.78 g) and iodomethane (1.21 mL) at 0□. After stirred for 14 h at room temperature, this reaction mixture was quenched with water. This mixture was extracted with diethyl ether, and combined organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting residue was chromatographed on silica gel (n-Hex:EtOAc=10:1 to 4:1) to afford the product as pale yellow oil. (89.1%)

Workup

  1. customthis reaction mixture was quenched with water
  2. extractionThis mixture was extracted with diethyl ether
  3. dry with materialwas dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was chromatographed on silica gel (n-Hex:EtOAc=10:1 to 4:1)

Sources & evidence

ORD record
ord-e99d042144a14f9eb6c190970c1e25dc
Source dataset
uspto-grants-2014_07
Patent number
US08785474B2

Reaction notes

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