반응 #40918

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Diisobutyl aluminium hydride

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

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

→

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

용매

toluene

반응 조건

후처리

1. 1
   기타The 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
   여과filtered through diatomaceous earth
5. 5
   세척The diatomaceous earth was washed twice with ethyl acetate
6. 6
   기타the aqueous solution was separated
7. 7
   추출extracted twice with ethyl acetate
8. 8
   세척The combined organic extracts were washed with saturated sodium chloride solution
9. 9
   건조dried over sodium sulfate
10. 10
    농축concentrated by evaporation in vacuo

실험 절차

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

출처