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

Participants

Reaction Steps

Diisobutyl aluminium hydride (1.5 M solution in toluene, 102 ml, 153 mmole) was added dropwise at −70° to −65° C. under argon to a solution of 1,4-dioxaspior[4.5]decane-8-carboxylic acid ethyl ester 4 (32.13 g, 150 mmole) in absolute toluene (160 ml), and stirred for 30 minutes. The reaction mixture was then quenched at −70° to −60° C. by adding methanol (80 ml). The reaction solution was heated to RT, saturated sodium chloride solution (100 ml) was added, and the reaction solution was suction filtered through diatomaceous earth. The diatomaceous earth was washed twice with ethyl acetate, and the aqueous solution was separated and extracted twice with ethyl acetate. The combined organic extracts were washed with saturated sodium chloride solution, dried over sodium sulfate, and concentrated by evaporation in vacuo.

Provenance & Evidence