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

HRID 728276Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 728276
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

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.).

Aufarbeitung

  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.)

Quellen und Nachweise

ORD-Eintrag
ord-3a81bea140744ec19e165b582c19053c
Quelldatensatz
uspto-grants-1991_09
Patentnummer
US05047432

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