関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Tert-Butylamine | HCID 6385 | — |
| 反応物 | (6-Bromopyridin-2-yl)methanol | HCID 3517811 | — |
| 反応物 | 4-Pentynoic acid, 1,1-dimethylethyl ester | HCID 10877341 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 触媒 | HCID 178418397 | HCID 178418397 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 生成物 | t-Butyl 5-(6-hydroxymethylpyridin-2-yl)pent-4-ynoate | HCID 58105203 | 56.9% |
反応手順
To a 200 mL round-bottom flask, 3.49 g of 2-bromopyridine-6-methanol, 3.0 g of t-butyl 4-pentynoate, 190 mg of BHT, 1.17 g of copper(I) iodide, 877 mg of tetrakis(triphenylphosphine)palladium(0), 2.72 g of t-butylamine and 56 mL of DMF were added, and the mixture was stirred under argon atmosphere at 80° C. for 6 hours. After the DMF was removed under reduced pressure from the reaction mixture, saturated aqueous sodium bicarbonate was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then the solvent was removed. The residue was purified by chromatography on silica gel (n-hexane-ethyl acetate=2:1) to give 2.76 g of t-butyl 5-(6-hydroxymethylpyridin-2-yl)pent-4-ynoate as a yellow oil.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US07834002B2 |
|---|
| 出典データセット | uspto-grants-2010_11 |
|---|
| ORD ID | ord-7e5a40fea3f542e6ad4cf74ba32c9a86 |
|---|
| 出典メモ | uspto-grants-2010_11 |
|---|
