Hydrochloric Acid → 4-Trimethylsilyl-3-cyanobutanoic acid

HRID 341337ノート

反応式

HRID 341337 の反応式
[CH3:1][Si:2]([CH3:14])([CH3:13])[CH2:3][CH:4]([C:11]#[N:12])[CH2:5][C:6]([O:8]CC)=[O:7].O.[OH-].[Li+].Cl>CO.COCCOC.O>[CH3:14][Si:2]([CH3:1])([CH3:13])[CH2:3][CH:4]([C:11]#[N:12])[CH2:5][C:6]([OH:8])=[O:7]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 71530807Ethyl 4-trimethylsilyl-3-cyanobutanoate

生成物 1

HCID 781006764-Trimethylsilyl-3-cyanobutanoic acid収率 99.5%

試薬・触媒・溶媒 1

HCID 86709899methanol DME water溶媒

実験手順

A solution of ethyl 4-(trimethylsilyl)-3-cyanobutanoate (341 mg, 1.60 mmol) in methanol/1,2-dimethoxyethane/water (3:2:1, 4.2 ml) was added with lithium hydroxide monohydrate (135 mg, 3.21 mmol), and the mixture was refluxed by heating for 1 hour with stirring. The reaction mixture was cooled on ice, and added with aqueous hydrochloric acid (1 N), and the mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous sodium sulfate, and the solvent was evaporated. The obtained crystals were purified by recrystallization, and the mother solution was subjected to purification by silica gel chromatography (2% methanol/chloroform) to obtain 4-trimethylsilyl-3-cyanobutanoic acid (295 mg, quant.) mentioned in the title as colorless scaly crystals.

後処理

  1. temperaturethe mixture was refluxed
  2. temperatureby heating for 1 hour
  3. temperatureThe reaction mixture was cooled on ice
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated
  8. customThe obtained crystals were purified by recrystallization
  9. customthe mother solution was subjected to purification by silica gel chromatography (2% methanol/chloroform)

出典と根拠

ORDレコード
ord-a7a9f8929a98436d842cc4977abb4bd5
出典データセット
uspto-grants-2014_11
特許番号
US08895769B2

反応ノート

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