Reacción #511796

Ecuación de reacción

Diisobutylaluminium hydride

1,4-dioxa-spiro[4.5]decane-8-carboxylic acid ethyl ester

→

1,4-Dioxa-spiro[4.5]decane-8-carbaldehyde

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe mixture was then quenched at −70 to −60° C. by addition of methanol (80 ml)
2. 2
   workup.ADDITIONsaturated sodium chloride solution (100 ml) was added
3. 3
   Filtraciónthe reaction solution was filtered out with suction over kieselguhr
4. 4
   LavadoThe kieselguhr was washed twice with ethyl acetate
5. 5
   Otrothe aqueous solution was separated off
6. 6
   Extracciónextracted twice with ethyl acetate
7. 7
   LavadoThe combined organic extracts were washed with saturated sodium chloride solution
8. 8
   Secadodried over sodium sulfate
9. 9
   Concentraciónconcentrated i

Procedimiento

Diisobutylaluminium hydride (1.5 M solution in toluene, 102 ml, 153 mmol) was added dropwise to a solution of 1,4-dioxa-spiro[4.5]decane-8-carboxylic acid ethyl ester (32.13 g, 150 mmol) in absol. toluene (160 ml) at −70 to −65° C. under argon and the mixture was stirred for 30 min. The mixture was then quenched at −70 to −60° C. by addition of methanol (80 ml). The reaction solution was warmed to RT, saturated sodium chloride solution (100 ml) was added and the reaction solution was filtered out with suction over kieselguhr. The 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 i. vac. Yield: 24.01 g (94%), yellow oil

Fuente