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Sodium Chloride → 5-(2,6-Dimethoxyphenyl)-1-(4-(trifluoromethoxy)benzyl)pyrrolidine-2,3-dione

HRID 594397
ノート
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反応式

HRID 594397 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH:11]1[CH:15](C(OCC)=O)[C:14](=[O:21])[C:13](=[O:22])[N:12]1[CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=1.[Na+].[Cl-]>CS(C)=O.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH:11]1[N:12]([CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]([F:32])([F:33])[F:34])=[CH:26][CH:25]=2)[C:13](=[O:22])[C:14](=[O:21])[CH2:15]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 2

HCID 5234Sodium ChlorideHCID 69082391Ethyl 2-(2,6-dimethoxyphenyl)-4,5-dioxo-1-(4-(trifluoromethoxy)-benzyl)pyrrolidine-3-carboxylate

生成物 1

HCID 690846265-(2,6-Dimethoxyphenyl)-1-(4-(trifluoromethoxy)benzyl)pyrrolidine-2,3-dione

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒2 回

実験手順

A mixture of ethyl 2-(2,6-dimethoxyphenyl)-4,5-dioxo-1-(4-(trifluoromethoxy)-benzyl)pyrrolidine-3-carboxylate (11.400 g; 23.68 mmol) and NaCl (2.767 g; 47.36 mmol) in DMSO (111 ml) and water (37 ml) was refluxed, under nitrogen, for 3 h. After cooling to rt, water (150 ml) was added, and the mixture was extracted with AcOEt (3×150 ml). The mixed organic layers were washed with brine (50 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Addition of Et2O and trituration allowed the precipitation of the product. Subsequent filtration, and drying of the obtained solid under HV afforded 5-(2,6-dimethoxyphenyl)-1-(4-(trifluoromethoxy)benzyl)pyrrolidine-2,3-dione as a pink solid. LC-MS (conditions A): tR=0.85 min.; [M+H]+: 410.15 g/mol.

後処理

  1. temperaturewas refluxed, under nitrogen, for 3 h
  2. extractionthe mixture was extracted with AcOEt (3×150 ml)
  3. washThe mixed organic layers were washed with brine (50 ml)
  4. dry with materialdried over anh. MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure
  7. additionAddition of Et2O and trituration
  8. customthe precipitation of the product
  9. filtrationSubsequent filtration
  10. customdrying of the obtained solid under HV

出典と根拠

ORDレコード
ord-8e1d897773b54a5eb88f0126f915acbc
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09242970B2

反応ノート

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