Sodium Thiosulfate → 2-(2,3-Dihydro-1-benzofuran-5-yl)-5-[[(3-fluorophenyl)sulfinyl]methyl]-1,3,4-oxadiazole

HRID 452706ノート

反応式

HRID 452706 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[O:11][C:12]([CH2:15][S:16][C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=4)=[N:13][N:14]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:32])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[O:11][C:12]([CH2:15][S:16]([C:17]4[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=4)=[O:32])=[N:13][N:14]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1

参加物

5

反応物 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 445904152-(2,3-Dihydro-1-benzofuran-5-yl)-5-[[(3-fluorophenyl)thio]methyl]-1,3,4-oxadiazole

生成物 1

HCID 686640712-(2,3-Dihydro-1-benzofuran-5-yl)-5-[[(3-fluorophenyl)sulfinyl]methyl]-1,3,4-oxadiazole収率 46%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of 2-(2,3-dihydro-1-benzofuran-5-yl)-5-[[(3-fluorophenyl)thio]methyl]-1,3,4-oxadiazole (0.25 g, 0.76 mmol) in acetonitrile (5 mL) was added m-chloroperbenzoic acid (70%, 0.18 g, 0.76 mmol) at 0° C., and the resulting mixture was stirred overnight at room temperature. A saturated aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1-2/1) and recrystallized from hexane/ethyl acetate to give the title compound (0.12 g, yield 46%) as colorless crystals.

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1-2/1)
  6. customrecrystallized from hexane/ethyl acetate

出典と根拠

ORDレコード
ord-0b3d1cc35a314f4988379407c06db728
出典データセット
uspto-grants-2013_07
特許番号
US08492378B2

反応ノート

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