반응 #2328972

반응 방정식

ammonium chloride

potassium-t-butoxide

methoxymethyltriphenylphosphonium chloride

methyl 4-oxocyclohexanecarboxylate

→

methyl 4-methoxymethylidenecyclohexanecarboxylate

수율 87.3%

용매

water

tetrahydrofuran

THF

반응 조건

후처리

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
   여과The precipitate was filtrated
7. 7
   세척washed again with 600 mL of hexane
8. 8
   세척the mixture was washed in turn with a mixed solution of methanol-water (1:1), water, and saturated solution
9. 9
   건조After dried over anhydrous sodium sulfate
10. 10
    workup.DISTILLATIONthe solvent was distilled off under reduced pressure

실험 절차

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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