Potassium Carbonate → HCID 54137616, compound

HRID 2286435Notes

Reaction equation

HRID 2286435 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[N:7][CH:8]=1.Br[CH:20]([CH3:27])[CH:21]=[CH:22][C:23]([O:25][CH3:26])=[O:24].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C.C(OCC)C>[F:18][C:2]([F:1])([F:17])[C:3]1[CH:4]=[CH:5][C:6]([O:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][CH:20]([CH3:27])[CH:21]=[CH:22][C:23]([O:25][CH3:26])=[O:24])=[CH:14][CH:15]=2)=[N:7][CH:8]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1552414-(5-Trifluoromethyl-pyridin-2-yloxy)-phenolHCID 54128087Methyl 4-bromo-2-pentenoate

Product 1

HCID 54137616HCID 54137616, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

In 50 ml of methyl ethyl ketone, 2.0 g (0.0078 mole) of 4-[5-(trifluoromethyl)-2-pyridinyloxy]phenol, 3.2 g of methyl 4-bromo-2-pentenoate, and 2.0 g of potassium carbonate were refluxed with constant stirring for 32 hours. Upon cooling to room temperature, the suspension was filtered through celite and the insoluble material washed with 75 ml of acetone. The filtrate was concentrated under reduced pressure to give an oily residue which was dissolved in 125 ml of ethyl ether and transferred to a separatory funnel. After washing with saturated sodium bicarbonate and water, the ether layer was dried over magnesium sulfate and charcoal filtered. Under reduced pressure, the solvent was evaporated and traces of volatile impurities removed at 0.4 mm Hg. (50° for 2 hours) to yield 2.4 g (84% ) of product, ND25 1.520.

Workup

  1. filtrationthe suspension was filtered through celite
  2. washthe insoluble material washed with 75 ml of acetone
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customto give an oily residue which
  5. customtransferred to a separatory funnel
  6. washAfter washing with saturated sodium bicarbonate and water
  7. dry with materialthe ether layer was dried over magnesium sulfate and charcoal
  8. filtrationfiltered
  9. customUnder reduced pressure, the solvent was evaporated
  10. customtraces of volatile impurities removed at 0.4 mm Hg

Sources & evidence

ORD record
ord-08a717429fa74a9b83e31aa43b42dc95
Source dataset
uspto-grants-1981_05
Patent number
US04266063

Reaction notes

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