تفاعل #449075

معادلة التفاعل

citric acid

(5-cyano-2-benzofuranyl)methyltriphenylphosphonium chloride

ethyl 2 -[4 -[((3S)-1-tert-butoxy-carbonyl-3-pyrrolidinyl)oxy]phenyl]-2-oxoacetate

tetrahydrofuran

sodium hydride

→

ethyl 2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]phenyl]-3-(5-cyano-2-benzofuranyl)acrylate

المذيبات

toluene ethyl acetate

ethanol

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGby stirring at room temperature for 1 hour
2. 2
   أخرىThe resulting reaction solution
3. 3
   استخلاصextracted with ethyl acetate
4. 4
   أخرىdried
5. 5
   workup.DISTILLATIONto distill off the solvent
6. 6
   أخرىThereafter, the residue thus obtained

الإجراء التجريبي

3.12 g of ethyl 2 -[4 -[((3S)-1-tert-butoxy-carbonyl-3-pyrrolidinyl)oxy]phenyl]-2-oxoacetate was dissolved in 100 ml of tetrahydrofuran, followed by the addition of 4.65 g of (5-cyano-2-benzofuranyl)methyltriphenylphosphonium chloride. To the thus prepared solution was added 400 mg of 60% sodium hydride. With stirring, to the resulting mixture was added dropwise 3 ml of ethanol, followed by stirring at room temperature for 1 hour. The resulting reaction solution was neutralized with 10% citric acid solution, extracted with ethyl acetate, and then dried to distill off the solvent. Thereafter, the residue thus obtained was subjected to silica gel column chromatography using a toluene/ethyl acetate mixture as an elution solvent, thereby obtaining 3.1 g of ethyl 2-[4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]phenyl]-3-(5-cyano-2-benzofuranyl)acrylate in the form of viscous oil as a mixture of E and Z forms. A portion of the thus obtained compound was separated into E and Z forms.

المصدر