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m-Chloroperbenzoic acid → 4-(3-fluorophenyl)-2,2-dimethyl-5-(4-(methylsulfinyl)phenyl)furan-3(2H)-one

HRID 2298317
ノート
印刷プレビュー

反応式

HRID 2298317 の反応式
[CH3:1][C:2]1([CH3:23])[C:6](=[O:7])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[C:4]([C:15]2[CH:20]=[CH:19][C:18]([S:21][CH3:22])=[CH:17][CH:16]=2)[O:3]1.ClC1C=C(C=CC=1)C(OO)=[O:29].C(=O)(O)[O-].[Na+]>ClCCl>[CH3:1][C:2]1([CH3:23])[C:6](=[O:7])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[C:4]([C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:22])=[O:29])=[CH:17][CH:16]=2)[O:3]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 183855844-(3-Fluorophenyl)-2,2-dimethyl-5-(4-(methylthio)phenyl)furan-3(2H)-one

生成物 1

HCID 183857244-(3-fluorophenyl)-2,2-dimethyl-5-(4-(methylsulfinyl)phenyl)furan-3(2H)-one収率 62%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of 2,2-dimethyl-4-(3-fluorophenyl)-5-{4-(methylthio)phenyl}-3(2H)-furanone (2.0 g, Example 166) in 50 ml dichloromethane, was added 1.5 g of m-chloroperoxybenzoic acid at 0° C. The reaction solution was stirred at the same temperature for one and half hours, after which 30 ml 5% aqueous sodium bicarbonate was added and the solution was stirred for another 10 minutes. Then the reaction mixture was concentrated in vacuo, and the resulting residue was extracted with 50 ml water and dichloromethane (30 ml×3). The organic layer was concentrated in vacuo and was purified by column chromatography (hexane/ethylacetate=1:1) to give 1.3 g of 2,2-dimethyl-4-(3-fluorophenyl)-5-{4-(methylsulfinyl)phenyl}-3(2H)-furanone. mp: 143-144° C. NMR: δ1.58 (s, 6H), 2.76(s, 3H), 7.26-7.08 (m, 3H), 7.30-7.38 (m, 1H), 7.65 (d, J=8.2 Hz, 2H), 7.80 (d, J=8.2 Hz, 2H).

後処理

  1. stirringthe solution was stirred for another 10 minutes
  2. concentrationThen the reaction mixture was concentrated in vacuo
  3. extractionthe resulting residue was extracted with 50 ml water and dichloromethane (30 ml×3)
  4. concentrationThe organic layer was concentrated in vacuo
  5. customwas purified by column chromatography (hexane/ethylacetate=1:1)

出典と根拠

ORDレコード
ord-44e221cb971b43b89b8c75788e542981
出典データセット
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06492416B1

反応ノート

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