反応 #336734

反応方程式

hydrochloric acid

tert.-butyl 4-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)-3-oxobutanoate

toluene

sodium methoxide

→

1-ethyl 6-tert.-butyl 2-hydroxy-4-oxoadipate

収率 89.6%

溶媒

ethanol

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture was stirred at 0° C. for 10 minutes
2. 2
   その他After evaporating off the most of the organic solvent under reduced pressure
3. 3
   抽出the mixture was extracted with ethyl acetate
4. 4
   洗浄washed with a saturated saline
5. 5
   乾燥dried over sodium sulfate
6. 6
   濃縮concentrated under reduced pressure

実験手順

To a solution of tert.-butyl 4-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)-3-oxobutanoate (16.30 g, 60.08 mmol) in a mixed solvent of toluene (120.0 ml) and ethanol (60.0 ml), sodium methoxide (4.91 g, 79.10 mmol) was dropwise added at 0° C. in an argon atmosphere and stirred for 30 minutes. After dropwise adding 1N hydrochloric acid (80.5 ml), the mixture was stirred at 0° C. for 10 minutes. After evaporating off the most of the organic solvent under reduced pressure, the mixture was extracted with ethyl acetate and washed with a saturated saline and a phosphate buffer (pH 7.0). The organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:acetone=2:1) to give pure 1-ethyl 6-tert.-butyl 2-hydroxy-4-oxoadipate (14.02 g, 53.85 mmol). Yield, 89.6%.

出典