Ethyl trimethylsilyl malonate → Ethyl 3-[2,4-dichloro-5-(2-chloro-4,6-difluorophenylamino)phenyl]-3-oxopropionate

HRID 749486ノート

反応式

HRID 749486 の反応式
C([Li])CCC.[C:6]([O:16][CH2:17][CH3:18])(=[O:15])[CH2:7][C:8]([O:10][Si](C)(C)C)=O.[Cl:19][C:20]1[CH:28]=[C:27]([Cl:29])[C:26]([NH:30][C:31]2[C:36]([F:37])=[CH:35][C:34]([F:38])=[CH:33][C:32]=2[Cl:39])=[CH:25][C:21]=1C(Cl)=O>CCCCCC.C(OCC)C.C(COC)OC.C(OCC)(=O)C>[Cl:19][C:20]1[CH:28]=[C:27]([Cl:29])[C:26]([NH:30][C:31]2[C:36]([F:37])=[CH:35][C:34]([F:38])=[CH:33][C:32]=2[Cl:39])=[CH:25][C:21]=1[C:8](=[O:10])[CH2:7][C:6]([O:16][CH2:17][CH3:18])=[O:15]

参加物

8

反応物 3

HCID 87655Ethyl trimethylsilyl malonateHCID 866002582,4-Dichloro-5-(2-chloro-4,6-difluorophenylamino)benzoyl chlorideHCID 178418339Butyllithium

生成物 1

HCID 68799347Ethyl 3-[2,4-dichloro-5-(2-chloro-4,6-difluorophenylamino)phenyl]-3-oxopropionate

試薬・触媒・溶媒 4

HCID 3283Diethyl Ether溶媒HCID 8058Hexane溶媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
-75 °C

実験手順

1.4 ml of a 1.6 M solution of butyllithium in hexane was added to a solution of 3.47 g (17.0 mmol) of ethyl trimethylsilyl malonate in 45 ml of diethyl ether at −75° C. in such a way that the temperature did not rise above −60° C. The mixture was then stirred at −75° C. for 30 minutes. The 2,4-dichloro-5-(2-chloro-4,6-difluorophenylamino)benzoyl chloride was dissolved in 45 ml of dimethoxyethane and added dropwise in 40 minutes. The mixture was slowly warmed to 10° C. and stirred at this temperature for 2.5 hours. The reaction mixture was diluted with ethyl acetate and washed twice each with 250 ml portions of water and saturated sodium bicarbonate solution. The organic phase was dried and concentrated. 3.88 g of the crude mixture were obtained and were reacted without further purification in the next stage.

後処理

  1. customdid not rise above −60° C
  2. additionadded dropwise in 40 minutes
  3. temperatureThe mixture was slowly warmed to 10° C.
  4. stirringstirred at this temperature for 2.5 hours
  5. washwashed twice each with 250 ml portions of water and saturated sodium bicarbonate solution
  6. customThe organic phase was dried
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-137ca073d3944f19b6d5b0a457ad8aa8
出典データセット
uspto-grants-2008_07
特許番号
US07402674B2

反応ノート

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