Ammonium Chloride → 1-(4-Methoxy-6-methylpyridin-2-yl)propan-2-one

HRID 1059862Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([CH3:10])[CH:4]=1.C([Li])CCC.CN(C)[C:18](=[O:20])[CH3:19].[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([CH2:10][C:18](=[O:20])[CH3:19])[CH:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 4-methoxy-2,6-dimethylpyridine (1.56 g) in tetrahydrofuran (15 ml) was added a solution of n-butyllithium in n-hexane (1.63M, 9.1 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 (1.59 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=2:1) to give 1-(4-methoxy-6-methylpyridin-2-yl)propan-2-one (1.75 g).

Workup

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

Sources & evidence

ORD record: ord-5b93b648ca8a46579800173fe47cd2cd
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06521643B1

Reaction notes

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