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Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → (2R)-1-(2,4-difluorophenyl)-2-hydroxypropan-1-one

HRID 1654197
ノート
印刷プレビュー

反応式

HRID 1654197 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:19])[C@H:10]([O:12]C1CCCCO1)[CH3:11].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:19])[C@H:10]([OH:12])[CH3:11]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 10199305(2R)-1-(2,4-difluorophenyl)-2-((tetrahydro-2H-pyran-2-yl)oxy)propan-1-one

生成物 1

HCID 9794084(2R)-1-(2,4-difluorophenyl)-2-hydroxypropan-1-one収率 74.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
55 °C

実験手順

In ethanol (3 ml) was dissolved (2R)-2',4'-difluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propiophenone (121 mg), to which was added pyridinium p-toluenesulfonate (25 mg), and the mixture was stirred for one hour at 55° C. The solvent was distilled off under reduced pressure, and the residue was dissolved in ethyl acetate (20 ml). The solution was washed with water and dried over anhydrous magnesium sulfate, followed by distilling off the solvent. The residue was purified by means of a silica gel chromatography (eluent: hexane-ethyl acetate=5:1) to give (2R)-2',4'-difluoro-2-hydroxypropiophenone (62 mg) as a pale yellow oily product. [α]D +68.7 (c=1.8 in chloroform)

後処理

  1. distillationThe solvent was distilled off under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate (20 ml)
  3. washThe solution was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationby distilling off the solvent
  6. customThe residue was purified by means of a silica gel chromatography (eluent: hexane-ethyl acetate=5:1)

出典と根拠

ORDレコード
ord-148157f537fd4a35bacc4db27fa6b91b
出典データセット
uspto-grants-1995_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05405861

反応ノート

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