Water → 1-[1-(4-Chlorophenyl)cyclobutyl]-3-ethyl-3-hydroxypentan-1-one oxime

HRID 728276ノート

反応式

HRID 728276 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][CH2:22][C:23](=[O:26])[CH2:24][CH3:25].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:23]([CH2:24][CH3:25])([OH:26])[CH2:22][CH3:21])[CH2:14][CH2:15][CH2:16]2)=[CH:11][CH:12]=1

参加物

7

反応物 4

HCID 962WaterHCID 7288Ethyl ketoneHCID 867439371-[1-(4-Chlorophenyl)cyclobutyl]ethanone oxime2 回HCID 178418339Butyllithium

生成物 1

HCID 867439391-[1-(4-Chlorophenyl)cyclobutyl]-3-ethyl-3-hydroxypentan-1-one oxime

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

A 2.7M solution of butyllithium in hexane (24 ml) was added under nitrogen to a stirred solution of 1-[1-(4-chlorophenyl)cyclobutyl]ethanone oxime [prepared as described in Example 84 (7.2 g)] in dry tetrahydrofuran (100 ml) over a period of 45 minutes whilst maintaining the temperature in the range -3° to 0° C. The mixture was stirred at 0° C. for 1 hour and then cooled to -5° C. A solution of dry pentan-3-one (3.4 ml) in dry tetrahydrofuran (10 ml) was added, the temperature of the mixture was allowed to rise to ambient and the mixture was stirred under nitrogen for 16 hours. The mixture was cooled to below 10° C. and water (100 ml) was added dropwise under nitrogen. The mixture was extracted with ether, the extracts dried and evaporated and the residue triturated with ice-cold petroleum ether (b.p. 40°-60° C.) to give 1-[1-(4-chlorophenyl)cyclobutyl]-3-ethyl-3-hydroxypentan-1-one oxime (m.p 113°-115° C.).

後処理

  1. temperaturewhilst maintaining the temperature in the range -3° to 0° C
  2. temperaturecooled to -5° C
  3. stirringwas stirred under nitrogen for 16 hours
  4. temperatureThe mixture was cooled to below 10° C.
  5. extractionThe mixture was extracted with ether
  6. customthe extracts dried
  7. customevaporated
  8. customthe residue triturated with ice-cold petroleum ether (b.p. 40°-60° C.)

出典と根拠

ORDレコード
ord-3a81bea140744ec19e165b582c19053c
出典データセット
uspto-grants-1991_09
特許番号
US05047432

反応ノート

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