Ammonium Chloride → 3-Chloro-2-methoxy-4,6-dimethylpyridine

HRID 1043894노트

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HRID 1043894 반응식
Br[C:2]1[C:3]([CH3:12])=[N:4][C:5]([O:10][CH3:11])=[C:6]([Cl:9])[C:7]=1[CH3:8].C([Li])CCC.[Cl-].[NH4+]>C1COCC1>[Cl:9][C:6]1[C:5]([O:10][CH3:11])=[N:4][C:3]([CH3:12])=[CH:2][C:7]=1[CH3:8]

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 866863283-Bromo-5-chloro-6-methoxy-2,4-dimethylpyridineHCID 178418339Butyllithium

생성물 1

HCID 866863293-Chloro-2-methoxy-4,6-dimethylpyridine수율 47.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

3-bromo-5-chloro-6-methoxy-2,4-dimethylpyridine (930 mg) was added to THF (10 mL). The solution was cooled to −78° C., and n-butyllithium (2.6 M solution in n-hexane, 1.428 mL) was added, followed by stirring at the same temperature for one hour. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with DCM. The organic layer was washed with brine and dried over sodium sulfate. The desiccant was removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 5% to 30%) to give the title compound (300 mg).

후처리

  1. extractionfollowed by extraction with DCM
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe desiccant was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/n-heptane, 5% to 30%)

출처 및 근거

ORD 기록
ord-6c64f2a183194f179e74453f3fed0a5a
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08563565B2

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