تفاعل #50256

معادلة التفاعل

Ethyl 2,3-di-oxo-1-azacyclodecane-10-carboxylate

t-Butyl dimethylphosphonoacetate

→

ethyl 3-t-butoxycarbonylmethylidene-2-oxo-1-azacyclodecane-10-carboxylate

المذيبات

toluene

THF

THF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONis added dropwise
2. 2
   أخرىis warned to room temperature
3. 3
   workup.STIRRINGthe reaction is stirred at room temperature for 2.5 hours
4. 4
   أخرىThe reaction is quenched with saturated ammonium chloride
5. 5
   استخلاصextracted several times with ethyl acetate
6. 6
   تجفيفThe combined organic layers are dried (MgSO4)
7. 7
   أخرىthe solvent is evaporated
8. 8
   أخرىThe product is purified by silica gel chromatography (30% ethyl acetate/hexane)

الإجراء التجريبي

Potassium hexamethyldisilylamide (40.5 mL of a 0.58M solution in toluene, 23.5 mmol) is added to THF (60 mL), and then cooled to 0° C. t-Butyl dimethylphosphonoacetate (4.6 mL, 23.5 mmol) is added dropwise, and the reaction is warned to room temperature and stirred for 25 minutes. Ethyl 2,3-di-oxo-1-azacyclodecane-10-carboxylate (2.83 g, 11.74 mmol) is added in THF (15 mL), and the reaction is stirred at room temperature for 2.5 hours. The reaction is quenched with saturated ammonium chloride, and then extracted several times with ethyl acetate. The combined organic layers are dried (MgSO4), and the solvent is evaporated. The product is purified by silica gel chromatography (30% ethyl acetate/hexane) to give ethyl 3-t-butoxycarbonylmethylidene-2-oxo-1-azacyclodecane-10-carboxylate.

المصدر