Ammonium Chloride → HCID 18630999, compound

HRID 1059867Notes

Reaction equation

HRID 1059867 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:11])=[N:5][CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C([Li])CCC.CN(C)[C:19](=[O:21])[CH3:20].[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH3:1][O:2][C:3]1[C:4]([CH2:11][C:19](=[O:21])[CH3:20])=[N:5][CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 31374DimethylacetamideHCID 6398793,4-Dimethoxy-2-methylpyridineHCID 178418339Butyllithium

Product 1

HCID 18630999HCID 18630999, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 3,4-dimethoxy-2-methylpyridine (1.53 g) in tetrahydrofuran (15 ml) was added a solution of n-butyllithium in n-hexane (1.63M, 7.36 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 (1.21 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 organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 50 g, 25% ethyl acetate in n-hexane) to give 1-(3,4-dimethoxypyridin-2-yl)propan-2-one (1.85 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 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 50 g, 25% ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-5fbc6f9c37c94cb1927f115ef3cc44b1
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Reaction notes

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