m-Chloroperbenzoic acid → 2-[3-(4-Cyanophenoxy)-2-hydroxy-3-methylbutyl]-pyrazine 1-oxide

HRID 1073959Notes

Reaction equation

HRID 1073959 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[OH:12][CH:13]([CH2:26][C:27]1[CH:32]=[N:31][CH:30]=[CH:29][N:28]=1)[C:14]([CH3:25])([CH3:24])[O:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1>ClCCl>[C:20]([C:19]1[CH:18]=[CH:17][C:16]([O:15][C:14]([CH3:24])([CH3:25])[CH:13]([OH:12])[CH2:26][C:27]2[CH:32]=[N:31][CH:30]=[CH:29][N+:28]=2[O-:9])=[CH:23][CH:22]=1)#[N:21]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 198956134-[2-Hydroxy-1,1-dimethyl-3-(2-pyrazinyl)propoxy]benzonitrile

Product 1

HCID 198956672-[3-(4-Cyanophenoxy)-2-hydroxy-3-methylbutyl]-pyrazine 1-oxideYield 30.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.18 g of m-chloroperbenzoic acid was added to a stirred solution of 0.28 g of 4-[2-hydroxy-1,1-dimethyl-3-(2-pyrazinyl)propoxy]benzonitrile in 10 ml of dichloromethane. After 16 hours a further 36 mg of m-chloroperbenzoic acid were added and the mixture was stirred for 24 hours. The solvents were then removed by evaporation and the residue was chromatographed on silica gel using diethyl ether/methanol (95:5) for the elution to give 0.09 g of 2-[3-(4-cyanophenoxy)-2-hydroxy- 3-methylbutyl]-pyrazine 1-oxide in the form of a white solid of melting point 103°-104° C. (from diethyl ether).

Workup

  1. customThe solvents were then removed by evaporation
  2. customthe residue was chromatographed on silica gel
  3. washfor the elution

Sources & evidence

ORD record
ord-c27cfe314e6d4adb838bff2c467d920e
Source dataset
uspto-grants-1990_11
Patent number
US04971982

Reaction notes

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