3-(2-(6,7-Difluoro-2-quinolinyl)ethenyl)benzaldehyde → 1-(3-(2-(6,7-Difluoro-2-quinolinyl)ethenyl)phenyl)-2-propen-1-ol

HRID 1755775노트

반응식

HRID 1755775 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]=[C:7]([CH:13]=[CH:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=[O:19])[CH:6]=[CH:5]2.[CH:23]([Mg]Br)=[CH2:24]>C1(C)C=CC=CC=1.C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]=[C:7]([CH:13]=[CH:14][C:15]1[CH:16]=[C:17]([CH:18]([OH:19])[CH:23]=[CH2:24])[CH:20]=[CH:21][CH:22]=1)[CH:6]=[CH:5]2

참가 물질

5

반응물 2

HCID 542979803-(2-(6,7-Difluoro-2-quinolinyl)ethenyl)benzaldehydeHCID 178418507HCID 178418507, 화합물

생성물 1

HCID 539422241-(3-(2-(6,7-Difluoro-2-quinolinyl)ethenyl)phenyl)-2-propen-1-ol수율 81%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

The aldehyde of Step 2 (35.93 g, 122 mmol) was suspended in 360 mL of toluene and cooled to 0° C. 1.0 M Vinylmagnesium bromide in THF (135 mL) was added into the addition funnel and the whole system was degassed by applying vacuum and flushed with nitrogen 3 times. The Grignard reagent was then added slowly at 0° C. and the mixture was stirred at 0° C. for 15 min. Cold 25% aq. NH4OAc was then added and the product was extracted in hot toluene, washed with brine, and dried over Na2SO4. The cloudy solution was filtered through celite, concentrated, and filtered through silica with EtOAc: toluene 10:90 to afford 32.04 g (81%) of the title product.

후처리

  1. customthe whole system was degassed
  2. customflushed with nitrogen 3 times
  3. additionThe Grignard reagent was then added slowly at 0° C.
  4. additionCold 25% aq. NH4OAc was then added
  5. extractionthe product was extracted in hot toluene
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationThe cloudy solution was filtered through celite,
  9. concentrationconcentrated
  10. filtrationfiltered through silica with EtOAc: toluene 10:90

출처 및 근거

ORD 기록
ord-fb58e4bd95484b5eaa115a04fe51ff4f
출처 데이터셋
uspto-grants-1995_08
특허 번호
US05438141

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