Sodium Hydroxide → HCID 67508942, compound

HRID 623492Notes

Reaction equation

HRID 623492 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])=[N:6][CH:7]=1.ClC1C=C(C=CC=1)C(OO)=[O:19].[OH-].[Na+]>ClCCl>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][C:10]([F:13])([F:11])[F:12])=[N+:6]([O-:19])[CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 23551655HCID 23551655, compound

Product 1

HCID 67508942HCID 67508942, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-methyl-2-(2,2,2-trifluoroethoxy)pyridine (0.55 g, 2.88 mmol, Step-1) and m-chloroperoxybenzoic acid (1.66 g, 5.77 mmol) in dichloromethane (50 mL) is stirred at room temperature for 20 hours. The reaction mixture is poured into 2M sodium hydroxide and extracted with ethyl acetate and dried over sodium sulfate and concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with ethyl acetate/methanol (10:1) to give 0.14 g (24% yield) of the title compound as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified by column chromatography on silica gel eluting with ethyl acetate/methanol (10:1)

Sources & evidence

ORD record
ord-83d8f043760e4a438c476b7dae8147bd
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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