Acetone → 1-[1-(4-Chlorophenyl)cyclobutyl]-3-hydroxy-3-methylbutan-1-one oxime

HRID 728272노트

반응식

HRID 728272 반응식
C([Li])CCC.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2([C:17](=[N:19][OH:20])[CH3:18])[CH2:16][CH2:15][CH2:14]2)=[CH:9][CH:8]=1.[CH3:21][C:22]([CH3:24])=[O:23].O>CCCCCC.O1CCCC1>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2([C:17](=[N:19][OH:20])[CH2:18][C:22]([OH:23])([CH3:24])[CH3:21])[CH2:14][CH2:15][CH2:16]2)=[CH:11][CH:12]=1

참가 물질

7

반응물 4

HCID 180AcetoneHCID 962WaterHCID 867439371-[1-(4-Chlorophenyl)cyclobutyl]ethanone oximeHCID 178418339Butyllithium

생성물 1

HCID 867439361-[1-(4-Chlorophenyl)cyclobutyl]-3-hydroxy-3-methylbutan-1-one oxime

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

반응 조건

온도
-5 °C

실험 절차

A 1.6M solution of butyllithium in hexane (55 ml) was added to a stirred solution of the 1-[1-(4-chlorophenyl)cyclobutyl]ethanone oxime (8.94 g) in dry tetrahydrofuran (120 ml) the temperature being maintained below 0° C. for 40 minutes. The mixture was cooled to -5° C. and acetone (2.67 ml) was added dropwise. The temperature of the reaction mixture was allowed to rise to ambient temperature over a period of 16 hours. The mixture was cooled to 10° C. and water (100 ml) was added and the resulting aqueous mixture was washed with ether. The aqueous layer was acidified with 5N sulphuric acid and an oil separated. The oil was dissolved in ether and the ether solution was washed with water, dried and evaporated to yield 1-[1-(4-chlorophenyl)cyclobutyl]-3-hydroxy-3-methylbutan-1-one oxime.

후처리

  1. temperaturebeing maintained below 0° C. for 40 minutes
  2. temperatureThe mixture was cooled to 10° C.
  3. washthe resulting aqueous mixture was washed with ether
  4. customan oil separated
  5. dissolutionThe oil was dissolved in ether
  6. washthe ether solution was washed with water
  7. customdried
  8. customevaporated

출처 및 근거

ORD 기록
ord-a60e239ea90e4884b6cffb64f9b742ce
출처 데이터셋
uspto-grants-1991_09
특허 번호
US05047432

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