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

HRID 1650954Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

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.).

Workup

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

Sources & evidence

ORD record: ord-e3931ae41fa44112bdc7a2258cc1512a
Source dataset: uspto-grants-1990_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04925879

Reaction notes

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