Water → 3-(2,3,4-Trimethoxy-6-methylbenzoyl)-4-trifluoromethyl-2-methoxy-5-methylpyridine

HRID 242427노트

반응식

HRID 242427 반응식
[CH3:1][Zn]C.[CH3:4][O:5][C:6]1[C:26]([O:27][CH3:28])=[C:25]([O:29][CH3:30])[CH:24]=[C:23]([CH3:31])[C:7]=1[C:8]([C:10]1[C:11]([O:21][CH3:22])=[N:12][CH:13]=[C:14](Br)[C:15]=1[C:16]([F:19])([F:18])[F:17])=[O:9].O>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:4][O:5][C:6]1[C:26]([O:27][CH3:28])=[C:25]([O:29][CH3:30])[CH:24]=[C:23]([CH3:31])[C:7]=1[C:8]([C:10]1[C:11]([O:21][CH3:22])=[N:12][CH:13]=[C:14]([CH3:1])[C:15]=1[C:16]([F:19])([F:18])[F:17])=[O:9]

참가 물질

6

반응물 3

HCID 962WaterHCID 230826073-(2,3,4-Trimethoxy-6-methylbenzoyl)-5-bromo-4-trifluoromethyl-2-methoxypyridineHCID 178477796HCID 178477796, 화합물

생성물 1

HCID 230825983-(2,3,4-Trimethoxy-6-methylbenzoyl)-4-trifluoromethyl-2-methoxy-5-methylpyridine수율 97.1%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매

실험 절차

3.80 ml (3.80 mmol) of dimethylzinc (1.0 mol/l hexane solution) was dropwise added at 0° C. to a solution having 0.60 g (1.29 mmol) of 3-(2,3,4-trimethoxy-6-methylbenzoyl)-5-bromo-4-trifluoromethyl-2-methoxypyridine obtained in Step (d) and 0.10 g (0.09 mmol) of tetrakis(triphenylphosphine)palladium dissolved in 10 ml of tetrahydrofuran, and the temperature was increased naturally, followed by stirring at room temperature for 8 days. Water was added to terminate the reaction, and tetrahydrofuran was distilled off under reduced pressure. After extraction with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate and subjected to filtration, and the solvent was distilled off under reduced pressure. The crude product was purified by silica gel column chromatography to obtain 0.50 g (yield: 96%) of 3-(2,3,4-trimethoxy-6-methylbenzoyl)-4-trifluoromethyl-2-methoxy-5-methylpyridine.

후처리

  1. temperaturethe temperature was increased naturally
  2. customto terminate
  3. customthe reaction, and tetrahydrofuran
  4. distillationwas distilled off under reduced pressure
  5. extractionAfter extraction with ethyl acetate
  6. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  7. filtrationsubjected to filtration
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe crude product was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-ee7eeadfaf514d27991e43906c9c3a45
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653113B2

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