O-(5-Chloro-thiophen-2-ylmethyl)-hydroxylamine → HCID 136058327, compound

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Reaction Steps

In this example, a mixture containing 4.0 gms (0.02 mol) of 5,5-dimethyl-3-hydroxy-2-propionylcyclohex-2-en-1-one and 3.6 gms (0.022 mol) of O-[(5-chlorothien-2-yl)methyl]hydroxylamine in 75 mls of ethanol was stirred at room temperature for about 12 hours. The mixture was then evaporated to remove the ethanol, affording a thick syrup. The syrup was then dissolved in methylene chloride and extracted twice with aqueous 5% wt. sodium hydroxide. The aqueous layer was separated and acidified with concentrated hydrochloric acid and then extracted twice with methylene chloride. The methylene chloride layer was separated, dried with magnesium sulfate, and filtered. The filtrate was evaporated under vacuum, affording a viscous liquid which was then purified via column chromatography eluting with tetrahydrofuran-hexane (1:2 vol. ratio) affording 4.8 gms of 2-{1-[(5-chlorothien-2-ylmethoxy)imino]propyl}-3-hydroxy-5,5-dimethylcyclohex-2-en-1-one.

Provenance & Evidence