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

HRID 1650951ノート

反応式

HRID 1650951 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
-5 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-33505a82fe51429ebbd990bc579e2b9a
出典データセット
uspto-grants-1990_05
特許番号
US04925879

反応ノート

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