Sodium Fluoride → 4-Methoxy-3-(2-methylphenoxy)-6-vinylpyridazine

HRID 1821683노트

반응식

HRID 1821683 반응식
Cl[C:2]1[N:7]=[N:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])=[C:4]([O:16][CH3:17])[CH:3]=1.[CH2:18]([Sn](CCCC)(CCCC)C=C)[CH2:19]CC.C(OCC)(=O)C.[F-].[Na+]>C1(C)C=CC=CC=1.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.O>[CH3:17][O:16][C:4]1[CH:3]=[C:2]([CH:18]=[CH2:19])[N:7]=[N:6][C:5]=1[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:15]

참가 물질

8

반응물 4

HCID 5235Sodium FluorideHCID 8857Ethyl AcetateHCID 81998TributylvinyltinHCID 229401366-Chloro-4-methoxy-3-(2-methylphenoxy)pyridazine

생성물 1

HCID 230140894-Methoxy-3-(2-methylphenoxy)-6-vinylpyridazine수율 88.6%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 1140Toluene용매

실험 절차

In toluene (2 mL) was dissolved 123 mg (0.490 mmol) of 6-chloro-4-methoxy-3-(2-methylphenoxy)pyridazine obtained in Example 2 (1), 246 mg (0.776 mmol) of tributyl-(vinyl)tin, and then, 119 mg (0.103 mmol) of tetrakis(triphenylphosphine)palladium were successively added to the solution at room temperature, and the resulting mixture was refluxed for 3 hours. The reaction mixture was allowed to stand for cooling, ethyl acetate (5 mL), water (3 mL) and sodium fluoride were added to the mixture, and the resulting mixture was stirred for 30 minutes and allowed to stand at at room temperature overnight. The mixture was filtered through Celite, ethyl acetate was added to the filtrate, then the organic layer was separated and washed with brine. After drying over anhydrous sodium sulfate, the solvent was removed. The obtained residue was purified by silica gel column chromatography (eluted with hexane:ethyl acetate=1:2) to obtain 105 mg (0.434 mmol, Yield: 88.6%) of 4-methoxy-3-(2-methylphenoxy)-6-vinylpyridazine.

후처리

  1. temperaturethe resulting mixture was refluxed for 3 hours
  2. temperaturefor cooling
  3. customto stand at at room temperature overnight
  4. filtrationThe mixture was filtered through Celite, ethyl acetate
  5. additionwas added to the filtrate
  6. customthe organic layer was separated
  7. washwashed with brine
  8. dry with materialAfter drying over anhydrous sodium sulfate
  9. customthe solvent was removed
  10. customThe obtained residue was purified by silica gel column chromatography (eluted with hexane:ethyl acetate=1:2)

출처 및 근거

ORD 기록
ord-ec9d9e7c44574f7a82f891040899bee8
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07608563B2

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