Ethyl Acetate → [3,4-Bis(4-methoxyphenyl)-1,2-oxazol-5-yl]acetonitrile

HRID 2260753Notes

Reaction equation

HRID 2260753 reaction equation
Cl[CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[C:4]=1[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1.[C-:24]#[N:25].[K+].C(OCC)(=O)C>CS(C)=O.O>[C:24]([CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[C:4]=1[C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)#[N:25]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 9032Potassium CyanideHCID 18998919HCID 18998919, compound

Product 1

HCID 13477021[3,4-Bis(4-methoxyphenyl)-1,2-oxazol-5-yl]acetonitrileYield 43.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A 500 mg of 5-chloromethyl-3,4-bis(4-methoxyphenyl)isoxazole was dissolved in a mixed solvent of dimethylsulfoxide (3 ml) and water (1 ml). To the solution, 122 mg of potassium cyanide was added, and the mixture was stirred at room temperature for 18 hours. A 80 ml of ethyl acetate was added to the mixture. The resulting mixture was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give 210 mg (yield 43.1%) of a desired 5-cyanomethyl-3,4-bis(4-methoxyphenyl)isoxazole.

Workup

  1. washThe resulting mixture was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-0fb518e494884a698fe599024447d9f5
Source dataset
uspto-grants-1995_12
Patent number
US05478856

Reaction notes

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