Water → HCID 57210891, compound

HRID 1589760Notes

Reaction equation

HRID 1589760 reaction equation
[H-].[Na+].[OH:3][C@@H:4]([CH3:23])[CH2:5][C@@H:6]([CH3:22])[O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1.[CH3:24]I.O>CN(C)C=O>[CH3:24][O:3][C@@H:4]([CH3:23])[CH2:5][C@@H:6]([CH3:22])[O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57000686HCID 57000686, compound

Product 1

HCID 57210891HCID 57210891, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

0.13 g of 55% sodium hydride was mixed with 1 ml of dimethylformamide. A solution of 0.56 g of the (R,S)-4-[4'-(3"-hydroxy-1"-methylbutoxy)phenyl]-benzonitrile prepared in the above Example 1 in 2 ml of dimethylformamide was added dropwise thereto under ice-cooling. The obtained mixture was then stirred at room temperature for one hour. Subsequently a solution of 0.36 g of methyl iodide in 2 ml of dimethylformamide was added thereto and the obtained mixture was stirred at room temperature for two hours. 10 ml of water was carefully added to the reaction mixture and the obtained mixture was extracted with diethyl ether. After thoroughly washing with water, drying and desolvating, the obtained residue was purified by silica gel column chromatography, similar to the case of Example 1, with the use of a mixture of n-hexane and ethyl acetate (4:1) as a developing solvent. Thus 0.36 g of the title compound, namely, (R,S)-4-[4'-(3"-methoxy-1"-methylbutoxy)phenyl]benzonitrile was obtained.

Workup

  1. additionwas added dropwise
  2. temperatureunder ice-cooling
  3. stirringthe obtained mixture was stirred at room temperature for two hours
  4. extractionthe obtained mixture was extracted with diethyl ether
  5. washAfter thoroughly washing with water
  6. customdrying
  7. customthe obtained residue was purified by silica gel column chromatography, similar to the case of Example 1, with the use of a mixture of n-hexane and ethyl acetate (4:1) as a developing solvent

Sources & evidence

ORD record
ord-8b5ee20f81e741f8af662e1658269e16
Source dataset
uspto-grants-1993_04
Patent number
US05200111

Reaction notes

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