Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → (2S)-2',4'-difluoro-2-hydroxypropiophenone

HRID 1654189ノート

反応式

HRID 1654189 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

4

反応物 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 10265121(2S)-1-(2,4-Difluorophenyl)-2-((tetrahydro-2H-pyran-2-yl)oxy)propan-1-one

生成物 1

HCID 10986991(2S)-2',4'-difluoro-2-hydroxypropiophenone収率 61.1%

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 (2S)-2',4'-difluoro-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propiophenone (95 mg), to which was added pyridinium p-toluenesulfonate (21 mg), followed by stirring for one hour at 55° C. The solvent was distilled off under reduced pressure, and the residue was dissolved in ethyl acetate (20 ml), which was 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 (2S)-2',4'-difluoro-2-hydroxypropiophenone (40 mg) as a pale yellow oily product.

後処理

  1. distillationThe solvent was distilled off under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate (20 ml)
  3. dry with materialwhich was dried over anhydrous magnesium sulfate
  4. distillationby distilling off the solvent
  5. 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-1fa21ef0d7f04c5c80985eaf1f3cca82
出典データセット
uspto-grants-1995_04
特許番号
US05405861

反応ノート

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