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

HRID 728272Notes

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][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

Participants

Conditions

Temperature: -5 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-a60e239ea90e4884b6cffb64f9b742ce
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05047432

Reaction notes

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