p-Toluenesulfonic acid → 1-Propanone, 1-(2,4-difluorophenyl)-2-[(tetrahydro-2H-pyran-2-YL)oxy]-,(2R)-

HRID 1654182ノート

反応式

HRID 1654182 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:13])[CH:10]([OH:12])[CH3:11].C1(C)C=CC(S(O)(=O)=O)=CC=1.[O:25]1[CH:30]=[CH:29][CH2:28][CH2:27][CH2:26]1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:13])[CH:10]([O:12][CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30][O:25]1)[CH3:11]

参加物

6

反応物 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 118301282',4'-Difluoro-2-hydroxypropiophenone

生成物 1

HCID 108693411-Propanone, 1-(2,4-difluorophenyl)-2-[(tetrahydro-2H-pyran-2-YL)oxy]-,(2R)-収率 97.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2',4'-Difluoro-2-hydroxypropiophenone (61 g) was dissolved in methylene chloride (500 ml), to which was added, under ice-cooling, p-toluene sulfonic acid.hydrate (1.0 g). To the mixture was added, under ice-cooling while stirring, 3,4-dihydro-2H-pyran (41.4 g) during 10 minutes. The mixture was stirred, under ice-cooling, for one hour, to which was added a 5% aqueous solution of sodium hydrogen carbonate (240 ml). The mixture was stirred for 10 minutes under ice-cooling. The methylene chloride layer was separated and dried over anhydrous magnesium sulfate, followed by distilling off the solvent. The residual oily product was purified by means of a silica gel column chromatography (hexane: ethyl acetate=5:1) to afford 2',4'-difluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propiophenone (86.5 g) as a pale yellow oily product.

後処理

  1. additionwas added, under ice-
  2. temperaturecooling
  3. additionTo the mixture was added, under ice-
  4. temperaturecooling
  5. stirringThe mixture was stirred, under ice-
  6. temperaturecooling, for one hour, to which
  7. stirringThe mixture was stirred for 10 minutes under ice-
  8. temperaturecooling
  9. customThe methylene chloride layer was separated
  10. dry with materialdried over anhydrous magnesium sulfate
  11. distillationby distilling off the solvent
  12. customThe residual oily product was purified by means of a silica gel column chromatography (hexane: ethyl acetate=5:1)

出典と根拠

ORDレコード
ord-470f5ff8c17b447f8c8e2ffbda035a00
出典データセット
uspto-grants-1995_04
特許番号
US05405861

反応ノート

読み込み中…