Hydrogen Peroxide → 2,2-Dimethyl-3-phenyl-cyclopropanecarboxylic acid amide

HRID 2240849노트

반응식

HRID 2240849 반응식
C(=O)([O-])[O-:2].[K+].[K+].[CH3:7][C:8]1([CH3:19])[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]1[C:17]#[N:18].OO>CS(C)=O.[Cl-].[Na+].O>[CH3:7][C:8]1([CH3:19])[CH:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:9]1[C:17]([NH2:18])=[O:2]

참가 물질

6

반응물 3

HCID 784Hydrogen Peroxide3회HCID 11430Potassium CarbonateHCID 134298982,2-Dimethyl-3-phenylcyclopropanecarbonitrile

생성물 1

HCID 576527872,2-Dimethyl-3-phenyl-cyclopropanecarboxylic acid amide

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
0 °C

실험 절차

Potassium carbonate (467 mg) was added to a solution of 2,2-dimethyl-3-phenyl-cyclopropanecarbonitrile (3/1 cis/trans mixture, 4 g, 23.4 mmol) in DMSO (7 mL). The resulting mixture was cooled to 0° C. and an aqueous solution of hydrogen peroxide (30%, 2.8 mL) was added. The reaction mixture was allowed to warm up to room temperature and was stirred overnight. A second aliquot of aqueous solution of hydrogen peroxide (30%, 2.8 mL) was added and the resulting mixture was stirred for 24 hours. A third aliquot of aqueous solution of hydrogen peroxide (30%, 3.0 mL) was added and the resulting mixture was stirred for 3 days. The reaction mixture was poured into brine and extracted with ethyl ether. The organic layer was separated, dried over Na2SO4, filtered, and evaporated under reduced pressure. The crude residue was purified by flash chromatography (0% to 65% of EtOAc in hexane) to give 2.66 of 2,2-dimethyl-3-phenyl-cyclopropanecarboxylic acid amide (2/1 trans/cis mixture), together with 1.125 g of starting material.

후처리

  1. temperatureto warm up to room temperature
  2. stirringthe resulting mixture was stirred for 24 hours
  3. stirringthe resulting mixture was stirred for 3 days
  4. extractionextracted with ethyl ether
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe crude residue was purified by flash chromatography (0% to 65% of EtOAc in hexane)

출처 및 근거

ORD 기록
ord-a84b4d5c25714a378f072e7ac14052ee
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07723391B2

반응 노트

불러오는 중…