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

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Reaction Steps

Diisobutylaluminium hydride (1.5 M solution in toluene, 102 ml, 153 mmol) was added dropwise at from −70 to −65° C., under argon, to a solution of 1,4-dioxa-spiro[4.5]decane-8-carboxylic acid ethyl ester 1 (32.13 g, 150 mmol) in abs. toluene (160 ml), and stirring was carried out for 30 minutes. The mixture was then quenched at from −70 to −60° C. by addition of methanol (80 ml). The reaction solution was heated to RT, saturated sodium chloride solution (100 ml) was added, and the reaction solution was filtered off with suction over kieselguhr. Kieselguhr was washed twice with ethyl acetate and the aqueous solution was separated off and extracted twice with ethyl acetate. The combined organic extracts were washed with saturated sodium chloride solution, dried over sodium sulfate and concentrated in vacuo.

Provenance & Evidence