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

Diisobutylaluminium hydride (1.5 M solution in toluene, 102 ml, 153 mmol) was added dropwise at −70 to −65° C., under argon, to a solution of 1,4-dioxa-spiro-[4.5]decane-8-carboxylic acid ethyl ester (32.13 g, 150 mmol) in abs. toluene (160 ml), and stirring was carried out for 30 min. The mixture was then quenched at −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 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.

1. customThe mixture was then quenched at −70 to −60° C. by addition of methanol (80 ml)
2. additionsaturated sodium chloride solution (100 ml) was added
3. filtrationthe reaction solution was filtered off with suction over kieselguhr
4. washKieselguhr was washed twice with ethyl acetate
5. customthe aqueous solution was separated
6. extractionextracted twice with ethyl acetate
7. washThe combined organic extracts were washed with saturated sodium chloride solution
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated in vacuo

ORD record

ord-94985f792ac0446fbc38082afbe620c4

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08119633B2