Trichloroacetic Acid → HCID 12137495, compound

HRID 985368Notes

Reaction equation

HRID 985368 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][CH:10](OCC)[O:11]CC)[N:5]=[C:4]([O:17][C:18]2[N:22]([CH3:23])[N:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[CH:3]=1.ClC(Cl)(Cl)C(O)=O>ClC(Cl)Cl.O.CCCCC.C(OCC)(=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]#[C:9][CH:10]=[O:11])[N:5]=[C:4]([O:17][C:18]2[N:22]([CH3:23])[N:21]=[C:20]([C:24]([F:27])([F:25])[F:26])[CH:19]=2)[CH:3]=1

Participants

6

Reactant 2

HCID 6421Trichloroacetic AcidHCID 12137494HCID 12137494, compound

Product 1

HCID 12137495HCID 12137495, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 22335286Ethyl acetate pentaneSolvent

Procedure

A suspension of 4-methyl-6-(3,3-diethoxyprop-1-ynyl) -2-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)pyridine (2.2 g, 5.7 mmol) in trichloromethane (100 ml), water (5 ml) and trichloroacetic acid (3 g) is heated overnight at reflux. After cooling, the reaction mixture is diluted with pentane:ethyl acetate 1:1 and the organic phase is washed with water and a saturated aqueous solution of sodium bicarbonate and dried. 40% of the product (0.7 g) is obtained by flash chromatography as nearly less crystals of mp 73° C.

Workup

  1. temperatureis heated overnight
  2. temperatureat reflux
  3. temperatureAfter cooling
  4. washthe organic phase is washed with water
  5. dry with materiala saturated aqueous solution of sodium bicarbonate and dried

Sources & evidence

ORD record
ord-c65f576017234caba87d7642fbe13048
Source dataset
uspto-grants-2005_03
Patent number
US06872690B2

Reaction notes

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