HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Hydrochloric Acid → 6-[3-Adamantan-1-yl-4-(tert-butyl-dimethyl-silanyloxy)-benzoyloxy]-nicotinic acid
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Hydrochloric Acid | HCID 313 | — |
| Edukt | Tributylstannane | HCID 5948 | — |
| Edukt | Allyl 6-[3-adamantan-1-yl-4-(tert-butyl-dimethyl-silanyloxy)-benzoyl-oxy]-nicotinate | HCID 21846704 | — |
| Katalysator | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Lösungsmittel | Tetrahydrofuran | HCID 8028 | — |
| Produkt | 6-[3-Adamantan-1-yl-4-(tert-butyl-dimethyl-silanyloxy)-benzoyloxy]-nicotinic acid | HCID 21846713 | 22,7% |
Reaktionsschritte
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.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US05726191 |
| Quelldatensatz | uspto-grants-1998_03 |
| ORD ID | ord-429d4cda5f5a43799ceb5fbb3c399100 |
| Quellennotiz | uspto-grants-1998_03 |