反応 #40914

反応方程式

Diisobutyl aluminium hydride

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

→

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

溶媒

toluene

反応条件

後処理

1. 1
   その他The 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
   ろ過filtered through diatomaceous earth
5. 5
   洗浄The diatomaceous earth was washed twice with ethyl acetate
6. 6
   その他the aqueous solution was separated
7. 7
   抽出extracted twice with ethyl acetate
8. 8
   洗浄The combined organic extracts were washed with saturated sodium chloride solution
9. 9
   乾燥dried over sodium sulfate
10. 10
    濃縮concentrated by evaporation in vacuo

実験手順

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.

出典