Reaktion #50256

Reaktionsgleichung

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

t-Butyl dimethylphosphonoacetate

→

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

Lösungsmittel

toluene

THF

THF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle