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Hydrochloric Acid → 6-[3-Adamantan-1-yl-4-(tert-butyl-dimethyl-silanyloxy)-benzoyloxy]-nicotinic acid
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Hydrochloric Acid | HCID 313 | — |
| 反応物 | Tributylstannane | HCID 5948 | — |
| 反応物 | Allyl 6-[3-adamantan-1-yl-4-(tert-butyl-dimethyl-silanyloxy)-benzoyl-oxy]-nicotinate | HCID 21846704 | — |
| 触媒 | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | 6-[3-Adamantan-1-yl-4-(tert-butyl-dimethyl-silanyloxy)-benzoyloxy]-nicotinic acid | HCID 21846713 | 22.7% |
反応手順
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.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US05726191 |
| 出典データセット | uspto-grants-1998_03 |
| ORD ID | ord-429d4cda5f5a43799ceb5fbb3c399100 |
| 出典メモ | uspto-grants-1998_03 |