反应 #2328972

反应方程式

ammonium chloride

potassium-t-butoxide

methoxymethyltriphenylphosphonium chloride

methyl 4-oxocyclohexanecarboxylate

→

methyl 4-methoxymethylidenecyclohexanecarboxylate

收率 87.3%

溶剂

water

tetrahydrofuran

THF

反应条件

后处理

1. 1
   workup.ADDITIONthe resulting solution added dropwise at −10 to 4° C. over 80 minutes
2. 2
   workup.STIRRINGAfter stirring at 0 to 4° C. for 60 minutes
3. 3
   workup.DISTILLATIONThe solvent of the reaction mixture was distilled off under reduced pressure and 600 mL of hexane
4. 4
   workup.ADDITIONwas added
5. 5
   workup.STIRRINGby stirring at room temperature for 30 minutes
6. 6
   过滤The precipitate was filtrated
7. 7
   洗涤washed again with 600 mL of hexane
8. 8
   洗涤the mixture was washed in turn with a mixed solution of methanol-water (1:1), water, and saturated solution
9. 9
   干燥After dried over anhydrous sodium sulfate
10. 10
    workup.DISTILLATIONthe solvent was distilled off under reduced pressure

实验过程

263.4 g of methoxymethyltriphenylphosphonium chloride was dispersed in 750 mL of tetrahydrofuran (THF) and 86.2 g of potassium-t-butoxide were added at −9 to −4° C. over 5 minutes. After stirring at −4 to −11° C. for 30 minutes, 100.0 g of methyl 4-oxocyclohexanecarboxylate was dissolved in 300 mL of THF and the resulting solution added dropwise at −10 to 4° C. over 80 minutes. After stirring at 0 to 4° C. for 60 minutes, 7.0 g of ammonium chloride and 20 mL of water were added. The solvent of the reaction mixture was distilled off under reduced pressure and 600 mL of hexane was added, followed by stirring at room temperature for 30 minutes. The precipitate was filtrated and the precipitate was suspended and washed again with 600 mL of hexane. After combining with the hexane filtrate, the mixture was washed in turn with a mixed solution of methanol-water (1:1), water, and saturated solution. After dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to obtain 103 g of methyl 4-methoxymethylidenecyclohexanecarboxylate as an oily substance.

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