Ammonium Chloride → HCID 18667482, compound

HRID 1059866Notes

Reaction equation

HRID 1059866 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][N:6]=[C:5]([CH3:11])[CH:4]=1.C([Li])CCC.CN(C)[C:19](=[O:21])[CH3:20].[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][N:6]=[C:5]([CH2:11][C:19](=[O:21])[CH3:20])[CH:4]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 31374DimethylacetamideHCID 186675994,5-Dimethoxy-2-methylpyridineHCID 178418339Butyllithium

Product 1

HCID 18667482HCID 18667482, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4,5-dimethoxy-2-methylpyridine (2.92 g) in tetrahydrofuran (30 ml) was added a solution of n-butyllithium in n-hexane (1.63M, 14 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 (2.31 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×4). 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=1:1) to give 1-(4,5-dimethoxypyridin-2-yl)propan-2-one (1.59 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×4)
  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=1:1)

Sources & evidence

ORD record
ord-cebfec73e0184cb89beafcdcec11764e
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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