Water → alpha-(p-Tolylthio)(m-phenoxyphenyl)-acetonitrile

HRID 1759420

반응식

HRID 1759420 반응식
[C:1]1([CH3:8])[CH:6]=[CH:5][C:4]([SH:7])=[CH:3][CH:2]=1.C[O-].[Na+].C1(C)C=CC(S(O[CH:22]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:26]=2)[C:23]#[N:24])(=O)=O)=CC=1.O>CO>[C:1]1([CH3:8])[CH:6]=[CH:5][C:4]([S:7][CH:22]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:26]=2)[C:23]#[N:24])=[CH:3][CH:2]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 78114-MethylbenzenethiolHCID 10942334Sodium MethoxideHCID 12945136O-(p-toluenesulfonyl)-m-phenoxymandelonitrile

생성물 1

HCID 12945139alpha-(p-Tolylthio)(m-phenoxyphenyl)-acetonitrile수율 100.7%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

p-Toluenethiol (5.00 g) was dissolved in 6 ml of methanol, and 1.60 ml of a 2.5 M methanol solution of sodium methoxide was added to the solution at room temperature in a stream of argon. The mixture was stirred under ice cooling. Then, 1.516 g of O-(p-toluenesulfonyl)-m-phenoxymandelonitrile was added, and the mixture was stirred for 30 minutes under ice cooling and then for 10 minutes at room temperature. Water (20 ml) was added, and the mixture was extracted with 30 ml of methylene chloride three times. The extract was washed with 20 ml of water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel; benzene) to afford 1.334 g (yield 100%) of alpha-(p-tolylthio)(m-phenoxyphenyl)acetonitrile as a colorless oil.

후처리

  1. stirringthe mixture was stirred for 30 minutes under ice cooling
  2. extractionthe mixture was extracted with 30 ml of methylene chloride three times
  3. washThe extract was washed with 20 ml of water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel; benzene)

출처 및 근거

ORD 기록
ord-489135cf672b4e8e8213b4db717ccb32
출처 데이터셋
uspto-grants-1982_07
특허 번호
US04340740

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