反应 #2122483

反应方程式

(2,4,5-trimethyl-phenyl)acetic acid methyl ester

4-hydroxy-1-methoxy-piperidine-4-carboxylic acid ethyl ester

potassium tert-butoxide

→

4-Hydroxy-8-methoxy-3-(2,4,5-trimethyl-phenyl)-1-oxa-8-aza-spiro[4.5]dec-3-en-2-one

溶剂

THF

THF

反应条件

后处理

1. 1
   其他The suspension obtained
2. 2
   温度refluxed under argon for one hour
3. 3
   温度After cooling to room temperature
4. 4
   浓缩the reaction mixture was concentrated
5. 5
   workup.ADDITIONwater was added
6. 6
   萃取The aqueous layer was extracted with dichloromethane
7. 7
   洗涤the combined organic layers were then washed with brine
8. 8
   干燥dried over sodium sulfate
9. 9
   过滤After filtration and concentration under vacuum
10. 10
    其他the residue was purified by column chromatography (silica gel, ethyl acetate 100%)

实验过程

To a solution of (2,4,5-trimethyl-phenyl)acetic acid methyl ester (0.6 g, 3.12 mmol) and 4-hydroxy-1-methoxy-piperidine-4-carboxylic acid ethyl ester (0.76 g, 3.74 mmol) in 7 ml anhydrous THF was added a 1 M solution of potassium tert-butoxide (6.9 ml, 8.87 mmol) in THF at room temperature. The suspension obtained was first stirred at room temperature for one hour, and then refluxed under argon for one hour. After cooling to room temperature, the reaction mixture was concentrated, water was added and the mixture acidified with little HCl (37%). The aqueous layer was extracted with dichloromethane, and the combined organic layers were then washed with brine and dried over sodium sulfate. After filtration and concentration under vacuum, the residue was purified by column chromatography (silica gel, ethyl acetate 100%). Yield: 280 mg of 4-hydroxy-8-methoxy-3-(2,4,5-trimethyl-phenyl)-1-oxa-8-aza-spiro[4.5]dec-3-en-2-one (title compound P2.2) as a white solid, mp 199-204° C.

来源