Water → Dibenzo[a,e]cyclopropa[c]cyclohepten-6(1H)-one, 1,1-difluoro-1a,10b-dihydro-

HRID 413954

反応式

HRID 413954 の反応式
Cl[C:2]([F:7])([F:6])[C:3]([O-])=O.[Na+].[CH:9]1[C:19]2[CH:18]=C[C:16]3[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=3[C:14](=[O:24])[C:13]=2[CH:12]=[CH:11][CH:10]=1.O>COCCOCCOC>[F:6][C:2]1([F:7])[CH:18]2[CH:3]1[C:23]1[CH:22]=[CH:21][CH:20]=[CH:16][C:15]=1[C:14](=[O:24])[C:13]1[CH:12]=[CH:11][CH:10]=[CH:9][C:19]=12

参加物

5

反応物 3

HCID 962WaterHCID 166795H-Dibenzo[a,d]cyclohepten-5-oneHCID 2734985Sodium chlorodifluoroacetate

生成物 1

HCID 12073911Dibenzo[a,e]cyclopropa[c]cyclohepten-6(1H)-one, 1,1-difluoro-1a,10b-dihydro-収率 45.1%

試薬・触媒・溶媒 1

HCID 8150Diglyme溶媒2 回

実験手順

A solution of sodium chlorodifluoroacetate (350 g) in diglyme (1400 mL) was added dropwise over 4 to 8 hours, preferably over 6 hours, to a solution of 5H-dibenzo[a,d]cyclo-hepten-5-one (25 g) in diglyme (500 mL), with stirring, and under nitrogen, maintaining the reaction temperature at 160°-165° C. The cooled reaction mixture was poured into water (1.8 L) and extracted with ether (1.8 L). The organic phase was washed with water, dried over sodium sulfate (Na2SO4), and evaporated. The residue was recrystallized from ethanol, then from acetone/hexane to give 14 g of 1,1-difluoro-1a,10b-dihydrodibenzo[a,e]cyclopropa[c]-cyclohepten-6(1H)-one.

後処理

  1. temperatureunder nitrogen, maintaining the reaction temperature at 160°-165° C
  2. customThe cooled reaction mixture
  3. extractionextracted with ether (1.8 L)
  4. washThe organic phase was washed with water
  5. dry with materialdried over sodium sulfate (Na2SO4)
  6. customevaporated
  7. customThe residue was recrystallized from ethanol

出典と根拠

ORDレコード
ord-3f71e71360174d3cbbbe18cf89673b84
出典データセット
uspto-grants-2003_05
特許番号
US06570016B1

関連ノート

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