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Trifluoroacetic acid → [5-Fluoro-2-methyl-3-(2-sulfobenzyl)indol-1-yl]acetic acid methyl ester

HRID 1944425
ノート
印刷プレビュー

反応式

HRID 1944425 の反応式
[CH3:1][O:2][C:3](=[O:16])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[CH:7]=[C:6]1[CH3:15].[Na+].[CH:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26]([O-:29])(=[O:28])=[O:27])=O.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCCl>[CH3:1][O:2][C:3](=[O:16])[CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[C:7]([CH2:18][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[S:26]([OH:29])(=[O:28])=[O:27])=[C:6]1[CH3:15]
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 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 3794540Sodium o-formylbenzenesulfonateHCID 58247161Methyl 2-(5-fluoro-2-methyl-1H-indol-1-yl)acetate

生成物 1

HCID 86652190[5-Fluoro-2-methyl-3-(2-sulfobenzyl)indol-1-yl]acetic acid methyl ester収率 73.6%

試薬・触媒・溶媒 1

HCID 11
1,2-Dichloroethane
溶媒
2 回

実験手順

A mixture of (5-fluoro-2-methylindol-1-yl)acetic acid methyl ester (1.0 g), 2-formylbenzensulfonic acid sodium salt (0.94 g) and 1,2-dichloroethane (15 mL) at 0° C. was treated dropwise with a mixture of triethylsilane (4.3 mL), trifluoroacetic acid (1.0 mL) and 1,2-dichloroethane (10 mL), and the resulting mixture was stirred at room temperature for 6 hours. The mixture was extracted with ethyl acetate and the combined organic extract was dried over sodium sulfate. The solvent was removed under reduced pressure and the residue purified by column chromatography on silica gel, eluting with a mixture of methanol and dichloromethane (0:1 to 1:9 by volume) to afford the title compound as a purple gum (1.3 g).

後処理

  1. extractionThe mixture was extracted with ethyl acetate
  2. extractionthe combined organic extract
  3. dry with materialwas dried over sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue purified by column chromatography on silica gel
  6. washeluting with a mixture of methanol and dichloromethane (0:1 to 1:9 by volume)

出典と根拠

ORDレコード
ord-e70b1af3948540bb810480d9cc1aec39
出典データセット
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08394836B2

反応ノート

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