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

HRID 1059863

반응식

HRID 1059863 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-0c8a7b8361f841a183aec70d59e1bb57
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06521643B1

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