Sodium Cyanide → Ethyl 3-(cyanomethyl)benzoate

HRID 1257447ノート

反応式

HRID 1257447 の反応式
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7].[C-:14]#[N:15].[Na+]>CSC.O>[C:14]([CH2:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])#[N:15]

参加物

5

反応物 2

HCID 8929Sodium CyanideHCID 14812190Ethyl 3-(chloromethyl)benzoate

生成物 1

HCID 83311Ethyl 3-(cyanomethyl)benzoate収率 89.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1068Dimethyl Sulfide溶媒

実験手順

To a solution of ethyl 3-(chloromethyl)benzoate (5.0 g, 25.1 mmol) in dimethylsulfide (50 mL) was added sodium cyanide (1.85 g, 37.8 mmol), and the mixture was stirred at room temperature for 15 hr. The reaction mixture was diluted with water, extracted with ethyl acetate, and the extract was washed successively with water and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate) to give the title compound (4.23 g, 89%) as a colorless oil.

後処理

  1. extractionextracted with ethyl acetate
  2. washthe extract was washed successively with water and saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (carrier: silica gel, eluent: hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-78727aa4f47b4393904f5fa9b1850504
出典データセット
uspto-grants-2013_06
特許番号
US08461348B2

反応ノート

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