Hydrochloric Acid → 1-[3-(Trifluoromethyl)pyridin-2-yl]ethan-1-one

HRID 2054329Notes

Reaction equation

HRID 2054329 reaction equation
C(C1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][CH:6]=[CH:5][N:4]=1)#N.[CH3:13][Mg]I.C([O:18][CH2:19][CH3:20])C.Cl>C1COCC1>[C:19]([C:20]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][CH:6]=[CH:5][N:4]=1)(=[O:18])[CH3:13]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 223215743-(Trifluoromethyl)pyridine-2-carbonitrileHCID 178418373HCID 178418373, compound

Product 1

HCID 534031371-[3-(Trifluoromethyl)pyridin-2-yl]ethan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 2-cyano-3-trifluoromethylpyridine (30.0 g, 0.174 moles) in anhydrous THF (200 mL) under N2 atmosphere and cool in an ice bath. Add drop wise 3.0 M MeMgI in diethyl ether (120 ml, 0.348 mol) to the reaction mixture and stir in an ice bath for 30 minutes. Pour the reaction mixture over ice cold water, acidify the mixture with 2.0 N aq. HCl to pH 2 to 3. Extract the reaction mixture with EtOAc (3×300 mL) and dry over anhydrous MgSO4. Filter, concentrate under vacuum to afford crude product. Purify the crude product by vacuum distillation to afford desired 2-acetyl-3-trifluoromethylpyridine as colorless oil.

Workup

  1. temperaturecool in an ice bath
  2. additionPour the reaction mixture over ice cold water
  3. extractionExtract the reaction mixture with EtOAc (3×300 mL)
  4. dry with materialdry over anhydrous MgSO4
  5. filtrationFilter
  6. concentrationconcentrate under vacuum
  7. customto afford crude product
  8. customPurify the crude product
  9. distillationby vacuum distillation

Sources & evidence

ORD record
ord-25992d00b1dc4ea3974e2a8ca6904dd4
Source dataset
uspto-grants-2008_02
Patent number
US07329664B2

Reaction notes

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