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

HRID 2240849ノート

反応式

HRID 2240849 の反応式
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]

参加物

6

反応物 3

HCID 784Hydrogen Peroxide3 回HCID 11430Potassium CarbonateHCID 134298982,2-Dimethyl-3-phenylcyclopropanecarbonitrile

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a84b4d5c25714a378f072e7ac14052ee
出典データセット
uspto-grants-2010_05
特許番号
US07723391B2

反応ノート

読み込み中…