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

HRID 413954

반응식

HRID 413954 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8150Diglyme용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3f71e71360174d3cbbbe18cf89673b84
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06570016B1

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