Trimethylsilyl cyanide → HCID 53403951、化合物

HRID 336825ノート

反応式

HRID 336825 の反応式
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:6]=1[F:12])=[O:4].C[Si]([C:17]#[N:18])(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C(#N)C.[Cl-].[Na+]>[F:12][C:6]1[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:5]=1[C:3](=[O:4])[CH2:2][C:17]#[N:18]

参加物

6

反応物 3

HCID 82115Trimethylsilyl cyanideHCID 2724141Tetrabutylammonium FluorideHCID 223137872-Bromo-1-(2-fluoro-4-hydroxyphenyl)ethanone

生成物 1

HCID 53403951HCID 53403951、化合物収率 62.4%

試薬・触媒・溶媒 2

HCID 5234Sodium Chloride溶媒HCID 6342Acetonitrile溶媒

実験手順

To a solution of 2.5 g (10.73 mmol) of 2-bromo-1-(2-fluoro-4-hydroxyphenyl)ethanone in 100 ml of acetonitrile are respectively added 1.2 g (11.8 mmol) of trimethylsilyl cyanide and 12.3 ml (12.3 mmol) of tetrabutyl-ammonium fluoride solution (1M in THF). The reaction mixture is stirred at room temperature for 16 h then diluted with an aqueous solution saturated with sodium chloride. The product is extracted several times with ethyl acetate. The organic phases are combined, dried over magnesium sulfate, filtered, then evaporated. The residue is purified by chromatography on silica (cyclohexane/ethyl acetate eluent: 5:5) to give 1.2 g (62%) of 3-(2-fluoro-4-hydroxyphenyl)-3-oxopropanenitrile in the form of a yellow solid.

後処理

  1. extractionThe product is extracted several times with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue is purified by chromatography on silica (cyclohexane/ethyl acetate eluent: 5:5)

出典と根拠

ORDレコード
ord-1eb2817b5b214bbdb5573717dbb5971b
出典データセット
uspto-grants-2014_11
特許番号
US08889711B2

反応ノート

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