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

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.

1. customThe batch was then quenched at −70 to −60° C. by addition of methanol (80 ml)
2. customthe reaction solution removed by suction filtration through diatomaceous earth
3. washThe diatomaceous earth was washed twice with ethyl acetate
4. customthe aqueous solution separated
5. extractionextracted twice with ethyl acetate
6. washThe combined organic extracts were washed with saturated sodium chloride solution
7. dry with materialdried over sodium sulfate
8. customevaporated under a vacuum

ORD record

ord-06978bf0ba6b4c049569616216655e79

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07589113B2