Water → HCID 18357786, compound

HRID 617388Notes

Reaction equation

HRID 617388 reaction equation
[CH3:1][C:2]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][C:13]#[N:14].[H-].[Na+].[CH2:22](I)[CH3:23].O>CN(C)C=O>[CH3:1][C:2]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:3]=1[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH:12]([CH2:22][CH3:23])[C:13]#[N:14]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 11118528HCID 11118528, compound

Product 1

HCID 18357786HCID 18357786, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-[2-(2,5-dimethylphenoxymethyl)-phenyl]acetonitrile (2.00 g, 8.0 mmol) in N,N-dimethyl-formamide (20 ml) was stirred at 0° C. 60% oily sodium hydride (0.38 g, 9.5 mmol) was added thereto, and then ethyl iodide (1.37 g, 8.8 mmol) was added dropwise over 5 minutes. After 1 hour, water was added, and the mixture was extracted with ethyl acetate, washed successively with water and saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=19/1) to give the desired compound 2-[2-(2,5-dimethylphenoxymethyl)phenyl]butyronitrile (1.91 g, 86%) as an oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed successively with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=19/1)

Sources & evidence

ORD record
ord-6ae4113e356d437e80f962d3e592b126
Source dataset
uspto-grants-1999_09
Patent number
US05948819

Reaction notes

Loading…