Tetrahydrofuran → HCID 3772327, compound

HRID 1645225Notes

Reaction equation

HRID 1645225 reaction equation
[O-]CC.[Na+].O1CCCC1.[C:10]([C:13]1[C:18]([Cl:19])=[CH:17][C:16]([C:20]([F:23])([F:22])[F:21])=[CH:15][N:14]=1)(=[O:12])[CH3:11].[F:24][C:25]([F:32])([F:31])[C:26](OCC)=[O:27]>O>[Cl:19][C:18]1[C:13]([C:10](=[O:12])[CH2:11][C:26](=[O:27])[C:25]([F:32])([F:31])[F:24])=[N:14][CH:15]=[C:16]([C:20]([F:22])([F:23])[F:21])[CH:17]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 9794Ethyl trifluoroacetateHCID 2723922Sodium ethoxideHCID 217121361-(3-Chloro-5-trifluoromethyl-pyridin-2-yl)-ethanone

Product 1

HCID 3772327HCID 3772327, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

608 mg of a sodium ethoxide 21% ethanol solution was added at 0° C. to a tetrahydrofuran (dehydrated) 9 mL solution of 1 g of 2-acetyl-3-chloro-5-(trifluoromethyl)pyridine and 635 mg of ethyl 2,2,2-trifluoroacetate, followed by stirring at room temperature for 13 hours. After completion of the reaction, water was added to the reaction liquid, followed by extraction with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 1.4 g of 1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-4,4,4-trifluorobutan-1,3-dione (after-mentioned intermediate No. IX-25).

Workup

  1. additionwas added to the reaction liquid
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-79ad4b602d2a42eeb48367943b2540fb
Source dataset
uspto-grants-2012_02
Patent number
US08124760B2

Reaction notes

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