Реакция #40914

Уравнение реакции

Diisobutyl aluminium hydride

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

→

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

Растворители

toluene

Условия реакции

Обработка

1. 1
   ДругоеThe reaction mixture was then quenched at −70° to −60° C.
2. 2
   workup.ADDITIONby adding methanol (80 ml)
3. 3
   workup.ADDITIONsaturated sodium chloride solution (100 ml) was added
4. 4
   Фильтрацияfiltered through diatomaceous earth
5. 5
   ПромывкаThe diatomaceous earth was washed twice with ethyl acetate
6. 6
   Другоеthe aqueous solution was separated
7. 7
   Экстракцияextracted twice with ethyl acetate
8. 8
   ПромывкаThe combined organic extracts were washed with saturated sodium chloride solution
9. 9
   Сушкаdried over sodium sulfate
10. 10
    Концентрированиеconcentrated by evaporation in vacuo

Методика

Diisobutyl aluminium hydride (1.5 M solution in toluene, 102 ml, 153 mmole) was added dropwise to a solution of 1,4-dioxa-spiro[4.5]decane-8-carboxylic acid ethyl ester 4 (32.13 g, 150 mmole) in absolute toluene (160 ml) at −70° to −65° C. under argon 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.

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