Sodium Cyanide → Ethyl 3-(cyanomethyl)benzoate

HRID 1257447노트

반응식

HRID 1257447 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

HCID 83311Ethyl 3-(cyanomethyl)benzoate수율 89.1%

시약·촉매·용매 2

HCID 962Water용매HCID 1068Dimethyl Sulfide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-78727aa4f47b4393904f5fa9b1850504
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461348B2

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