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 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.

1. customThe mixture was then quenched at from −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 off
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-02cbccaca9ed49829129509f3db1f3b5

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08058475B2