Triethylamine → Methyl 4-(cyanomethyl)benzoate

HRID 352744

反応式

HRID 352744 の反応式
O[CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1.[CH2:13]([N:15](CC)CC)C.CS(Cl)(=O)=O>ClCCl>[C:13]([CH2:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)#[N:15]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 81325Methyl 4-(hydroxymethyl)benzoate

生成物 1

HCID 848548Methyl 4-(cyanomethyl)benzoate収率 86%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

In dichloromethane (20 ml), methyl 4-hydroxymethylbenzoate (1.00 g) was dissolved, followed by the addition of triethylamine (0.9 ml). Under ice cooling, a solution of methanesulfonyl chloride (0.70 g) in dichloromethane (dichloromethane: 5 ml) was added to the resulting solution. The resulting mixture was stirred at room temperature for 15 hours. After dilution with dichloromethane, the reaction mixture was washed with water and was then dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was dissolved in acetonitrile (12 ml). To the resulting solution, potassium cyanide (0.80 g) and 18-Crown-6 (0.16 g) were added, followed by stirring at room temperature for 40 hours. After concentration under reduced pressure, the concentrate was diluted with dichloromethane, washed with water and then, dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by chromatography on a silica gel column (dichloromethane), whereby colorless crystals (0.91 g, 86%) was obtained. A portion of the resulting crystals was recrystallized from a mixed solvent of hexane and ethyl acetate, whereby colorless crystals were obtained.

後処理

  1. washAfter dilution with dichloromethane, the reaction mixture was washed with water
  2. dry with materialwas then dried over anhydrous sodium sulfate
  3. customThe residue obtained
  4. distillationby distilling off the solvent under reduced pressure
  5. dissolutionwas dissolved in acetonitrile (12 ml)
  6. additionTo the resulting solution, potassium cyanide (0.80 g) and 18-Crown-6 (0.16 g) were added
  7. stirringby stirring at room temperature for 40 hours
  8. concentrationAfter concentration under reduced pressure
  9. additionthe concentrate was diluted with dichloromethane
  10. washwashed with water
  11. dry with materialdried over anhydrous sodium sulfate
  12. customThe residue obtained
  13. distillationby distilling off the solvent under reduced pressure
  14. customwas purified by chromatography on a silica gel column (dichloromethane)

出典と根拠

ORDレコード
ord-26fdc3ba4fff4937bd3baaf735409014
出典データセット
uspto-grants-2004_06
特許番号
US06747023B1

関連ノート

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