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2,3-Dihydrofuran → 4-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2-tetrahydrofuranyl) benzoic acid amide

HRID 552642
ノート
印刷プレビュー

反応式

HRID 552642 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:27])([F:26])[F:25])[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH2:20])=[O:19])=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[O:28]1[CH:32]=[CH:31][CH2:30][CH2:29]1.C(=O)([O-])O.[Na+]>ClCCl.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:24]([F:25])([F:27])[F:26])[O:13][N:12]=[C:11]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH:20][CH:29]4[CH2:30][CH2:31][CH2:32][O:28]4)=[O:19])=[C:16]([CH3:23])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 709342,3-DihydrofuranHCID 516892Sodium BicarbonateHCID 667845734-(5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-2-methylbenzamide

生成物 1

HCID 252170264-[5-(3,5-Dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl-N-(2-tetrahydrofuranyl) benzoic acid amide収率 80.8%

試薬・触媒・溶媒 2

HCID 521998
p-Toluenesulfonic acid monohydrate
触媒
HCID 6344Dichloromethane溶媒

実験手順

In a solution of 1.25 g of 4-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-methyl benzoic acid amide synthesized in Step 1 of Synthetic Example 19 and 0.32 g of 2,3-dihydrofuran in 30 mL of dichloromethane, 0.01 g of p-toluene sulfonic acid monohydrate was added at room temperature with stirring, and stirred at room temperature for 3 days. After the completion of the reaction, 30 mL of saturated sodium hydrogen carbonate aqueous solution was added in the reaction mixture, extracted with ethyl acetate (30 mL×2), the organic phase was dehydrated with and dried over saturated sodium chloride aqueous solution and then anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified with silica gel column chromatography that was eluated with ethyl acetate-hexane (1:1) to obtain 1.18 g of the aimed product as colorless resinous substance.

後処理

  1. stirringstirred at room temperature for 3 days
  2. additionwas added in the reaction mixture
  3. extractionextracted with ethyl acetate (30 mL×2)
  4. dry with materialdried over saturated sodium chloride aqueous solution
  5. distillationanhydrous sodium sulfate, and the solvent was distilled off under reduced pressure
  6. customThe residue was purified with silica gel column chromatography that

出典と根拠

ORDレコード
ord-6fa8cb8356db42518a6edce3413f5096
出典データセット
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07951828B1

反応ノート

読み込み中…

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