18-Crown-6 → HCID 86658558、化合物

HRID 1520204ノート

反応式

HRID 1520204 の反応式
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13](=[O:16])[CH2:14]Br)[CH:10]=[N:9]2)=[CH:5][CH:4]=1.[F-:19].[K+].C1OCCOCCOCCOCCOCCOC1>C(#N)C>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13](=[O:16])[CH2:14][F:19])[CH:10]=[N:9]2)=[CH:5][CH:4]=1

参加物

5

反応物 3

HCID 2855718-Crown-6HCID 522689Potassium FluorideHCID 866423312-Bromo-1-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)ethanone

生成物 1

HCID 86658558HCID 86658558、化合物収率 78%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

According to Scheme 6 Step 1: A solution of 1-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-2-bromoethanone (8.39 mmol, 3.00 g), KF (33.6 mmol, 1.97 g) and 18-crown-6 (4.20 mmol, 1.12 g) in acetonitrile (25 mL) was stirred under reflux for 3 hours. After the evaporation of solvent, the crude residue was dissolved in AcOEt. The organic phase was washed with water, was dried over Na2SO4, was filtered and was concentrated. The resulting crude product was purified by flash chromatography over silica gel using DCM/MeOH (100:0 to 95:5) as eluent to yield 1-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-2-fluoroethanone (3.62 mmol, 900 mg, 78%) as a white solid.

後処理

  1. temperatureunder reflux for 3 hours
  2. customAfter the evaporation of solvent
  3. dissolutionthe crude residue was dissolved in AcOEt
  4. washThe organic phase was washed with water
  5. dry with materialwas dried over Na2SO4
  6. filtrationwas filtered
  7. concentrationwas concentrated
  8. customThe resulting crude product was purified by flash chromatography over silica gel

出典と根拠

ORDレコード
ord-4ce6190fff7a4f37b1ba1b76a7d7e80d
出典データセット
uspto-grants-2015_07
特許番号
US09073907B2

反応ノート

読み込み中…