Reaktion #1739

Reaktionsgleichung

tributyltin hydride

ester

allyl 6-[3-adamantan-1 -yl-4-(tert-butyl-dimethyl-silanyloxy)-benzoyl-oxy]-nicotinate

hydrochloric acid

→

6-[3-adamantan-1-yl-4-(tert-butyl-dimethyl-silanyloxy)-benzoyloxy]-nicotinic acid

Ausbeute 22.7%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONthe reaction mixture was poured on to ice/saturated ammonium chloride solution
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   SonstigeThe dark oil obtained
4. 4
   Sonstigeafter drying
5. 5
   Sonstigeevaporation
6. 6
   Sonstigewas purified by chromatography (RP18-LiChroprep, acetonitrile) and recrystallization from ethyl acetate

Vorschrift

100 mg of this ester were dissolved in 5 ml of absolute tetrahydrofuran and treated under argon with 104 mg of tetrakis-(triphenylphosphine)-palladium and 61 mg of tributyltin hydride. After stirring at room temperature for 30 min., the reaction mixture was poured on to ice/saturated ammonium chloride solution, acidified with 1N hydrochloric acid and extracted with ethyl acetate. The dark oil obtained after drying and evaporation was purified by chromatography (RP18-LiChroprep, acetonitrile) and recrystallization from ethyl acetate. There were obtained 21 mg of 6-[3-adamantan-1-yl-4-(tert-butyl-dimethyl-silanyloxy)-benzoyloxy]-nicotinic acid in colorless crystals, m.p. 188°-190° C.

Quelle