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

HRID 1755775ノート

反応式

HRID 1755775 の反応式
[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

参加物

5

反応物 2

HCID 542979803-(2-(6,7-Difluoro-2-quinolinyl)ethenyl)benzaldehydeHCID 178418507HCID 178418507、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fb58e4bd95484b5eaa115a04fe51ff4f
出典データセット
uspto-grants-1995_08
特許番号
US05438141

反応ノート

読み込み中…