反応 #5501

反応方程式

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

t-Butyl dimethylphosphonoacetate

→

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

溶媒

toluene

THF

THF

反応条件

後処理

1. 1
   workup.ADDITIONis added dropwise
2. 2
   workup.STIRRINGthe reaction is stirred at room temperature for 2.5 hours
3. 3
   その他The reaction is quenched with saturated ammonium chloride
4. 4
   抽出extracted several times with ethyl acetate
5. 5
   乾燥The combined organic layers are dried (MgSO4)
6. 6
   その他the solvent is evaporated
7. 7
   その他The product is purified by silica gel chromatography (30% ethyl acetate/hexane)

実験手順

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 warmed 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.

出典