Dimethylacetamide → 1-(5-Chloropyridin-2-yl)ethan-1-one

HRID 1437268Notes

Reaction equation

HRID 1437268 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][N:8]=1.CN(C)[C:16](=[O:18])[CH3:17]>CCCCCC.C(OCC)C>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([C:16](=[O:18])[CH3:17])=[N:8][CH:9]=1

Participants

6

Reactant 3

HCID 31374DimethylacetamideHCID 8170982-Bromo-5-chloropyridineHCID 178418339Butyllithium

Product 1

HCID 101541661-(5-Chloropyridin-2-yl)ethan-1-one

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

Under cooling at −78° C., 1.56M n-butyllithium in hexane (27 mL) was added dropwise to 2-bromo-5-chloropyridine (6.8 g) in diethyl ether (45 mL), and then N,N-dimethylacetamide (5 mL) was added dropwise thereto, followed by stirring for 30 minutes. The reaction mixture was partitioned by use of saturated aqueous ammonium chloride and ethyl acetate. The organic layer was dried over sodium sulfate anhydrate, followed by filtration. The solvent was removed under reduced pressure, and the residue was purified through silica gel column chromatography (hexane-ethyl acetate), to thereby give 1-(5-chloro-2-pyridyl)ethanone as a solid (3.26 g, 59%).

Workup

  1. customThe reaction mixture was partitioned by use of saturated aqueous ammonium chloride and ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate anhydrate
  3. filtrationfollowed by filtration
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified through silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-54878bc4476e4bd69c7dbfe10a028619
Source dataset
uspto-grants-2009_11
Patent number
US07622471B2

Reaction notes

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