Ethyl 1,4-dioxaspiro(4.5)decane-8-carboxylate → 1,4-Dioxaspiro(4.5)decane-8-carbaldehyde

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Reaction Steps

A solution of 1,4-dioxaspiro[4.5]decane-8-carboxylic acid ethyl ester (32.13 g, 150 mmol) in absol. toluene (160 ml) was combined dropwise at −70 to −65° C. under argon with diisobutylaluminium hydride (1.5 M solution in toluene, 102 ml, 153 mmol) and stirred for 30 min. The batch was then quenched at −70 to −60° C. by addition of methanol (80 ml). The reaction solution was heated to RT, combined with saturated sodium chloride solution (100 ml) and the reaction solution removed by suction filtration through diatomaceous earth. The diatomaceous earth was washed twice with ethyl acetate, the aqueous solution separated and extracted twice with ethyl acetate. The combined organic extracts were washed with saturated sodium chloride solution, dried over sodium sulfate and evaporated under a vacuum.

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