Ammonium Chloride → 1-(4-Methoxypyridin-2-yl)propan-2-one

HRID 1059863

Reaction equation

HRID 1059863 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N:3]=1.C([Li])CCC.CN(C)[C:17](=[O:19])[CH3:18].[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH3:9][O:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([CH2:1][C:17](=[O:19])[CH3:18])[CH:7]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 31374DimethylacetamideHCID 47377584-Methoxy-2-methylpyridineHCID 178418339Butyllithium

Product 1

HCID 186310011-(4-Methoxypyridin-2-yl)propan-2-one

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2-methyl-4-methoxypyridine (2.03 g) in tetrahydrofuran (20 ml) was added a solution of n-butyllithium in n-hexane (1.63M, 12.1 ml) dropwise at −50° C. under a nitrogen atmosphere, and the mixture was warmed to 0° C. The mixture was cooled to −50° C., and N,N-dimethylacetamide (1.99 ml) was added dropwise. Then the mixture was warmed to room temperature, poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate (100 ml×2). The combined organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 100 g, n-hexane:ethyl acetate=1:2) to give 1-(4-methoxypyridin-2-yl)propan-2-one (2.35 g).

Workup

  1. temperatureThe mixture was cooled to −50° C.
  2. temperatureThen the mixture was warmed to room temperature
  3. extractionextracted with ethyl acetate (100 ml×2)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography (silica gel 100 g, n-hexane:ethyl acetate=1:2)

Sources & evidence

ORD record
ord-0c8a7b8361f841a183aec70d59e1bb57
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Linked notes

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