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1,1-Dichloroethane → [3-(3-Benzenesulfonylthiophen-2-ylmethyl)-5-chloro-2-methylindol-1-yl]acetic acid methyl ester

HRID 1944454
ノート
印刷プレビュー

反応式

HRID 1944454 の反応式
C([SiH](CC)CC)C.FC(F)(F)C(O)=O.ClC(Cl)C.[CH3:19][O:20][C:21](=[O:34])[CH2:22][N:23]1[C:31]2[C:26](=[CH:27][C:28]([Cl:32])=[CH:29][CH:30]=2)[CH:25]=[C:24]1[CH3:33].[C:35]1([S:41]([C:44]2[CH:48]=[CH:47][S:46][C:45]=2[CH:49]=O)(=[O:43])=[O:42])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(=O)([O-])O.[Na+]>[CH3:19][O:20][C:21](=[O:34])[CH2:22][N:23]1[C:31]2[C:26](=[CH:27][C:28]([Cl:32])=[CH:29][CH:30]=2)[C:25]([CH2:49][C:45]2[S:46][CH:47]=[CH:48][C:44]=2[S:41]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)(=[O:43])=[O:42])=[C:24]1[CH3:33]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 63651,1-Dichloroethane2 回HCID 6422Trifluoroacetic acid2 回HCID 12052Triethylsilane2 回HCID 9162623-Benzenesulfonylthiophene-2-carbaldehydeHCID 60074868Methyl 2-(5-chloro-2-methyl-1H-indol-1-yl)acetate

生成物 1

HCID 67044072
[3-(3-Benzenesulfonylthiophen-2-ylmethyl)-5-chloro-2-methylindol-1-yl]acetic acid methyl ester
収率 76.6%

試薬・触媒・溶媒 1

HCID 516892Sodium Bicarbonate溶媒

実験手順

A mixture of triethylsilane (2.7 g), trifluoroacetic acid (1.6 g) and dichloroethane (8.0 mL) at −20° C. was treated dropwise with a mixture of (5-chloro-2-methylindol-1-yl)acetic acid methyl ester (0.36 g), 3-phenylsulphony-2-thiophenealdehyde (0.39 g) and dichloroethane (8.0 mL), and the resulting mixture was warmed to room temperature over a period of 1.5 hours. The mixture was treated with additional triethylsilane (2.7 g) and trifluoroacetic acid (1.6 g) and then stirred at room temperature for 1 hour. The mixture was diluted with saturated aqueous sodium hydrogen carbonate solution and extracted with dichloromethane. The combined organic extract was washed with saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and ethyl acetate (1:0 to 0:1 by volume) to afford the title compound (0.55 g).

後処理

  1. extractionextracted with dichloromethane
  2. extractionThe combined organic extract
  3. washwas washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluting with a mixture of dichloromethane and ethyl acetate (1:0 to 0:1 by volume)

出典と根拠

ORDレコード
ord-2f9363e2d6da42bbb4a34113abcb8edb
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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