Methanol → 1-Hydroxy-3-(3-ethyl-1-methylcyclobutyl)-prop-1-en-3-one

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Sodium hydride (1.25 g of 50% mineral oil dispersion, 50 mmol) was washed with dry hexane and then stirred under an argon atmosphere with 12.5 ml of dry ether. A solution of 5 ml of methyl formate and 2.4 g of (1-methyl-3-ethylcyclobutyl) methyl ketone (prepared in Example 3A) in 5 ml of ether was then added to the reaction mixture along with about 0.5 ml of methanol. As a voluminous precipitate formed, sufficient ether was added to make the reaction mixture more easily stirred. The resultant mixture was stirred for 1 hr and then quenched by the addition of water. The ether phase was separated and extracted three times with 1 M sodium hydroxide. The combined aqueous extraction phases were acidified with concentrated hydrochloric acid and extracted three times with ether. The combined ether extract was evaporated in vacuo. Traces of water were removed by twice addition of benzene which was removed by evaporation in vacuo. The title compound had the following physical characteristics:

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