関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Triethylamine | HCID 8471 | — |
| 反応物 | 1-Undecyne | HCID 75249 | — |
| 反応物 | 6-Bromopyridine-2-carbaldehyde | HCID 2757009 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 触媒 | Dichlorobis(triphenylphosphine)palladium | HCID 6102075 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | 6-(1-Undecynyl)pyridine-2-carboxaldehyde | HCID 15380646 | 84.3% |
反応手順
A solution of 6-bromopyridine-2-caboxaldehyde (15.0 g), 1-undecyne (12.9 g), triethylamine (24.5 g), bis(triphenylphosphine)palladium(II)chloride (1.1 g, 2%), and copper(I)iodide (0.15 g, 1%) in dry tetrahydrofuran (60 ml) was heated under nitrogen at 55° C. for 10 hrs. The reaction mixture was filtered, the filter cake was washed with ethyl acetate, and the filtrate was evaporated. The residue was dissolved in ethyl acetate, and the solution was washed with half-saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was flash chromatographed on silica gel, eluting with 0%-2%-ethyl acetate:hexane. The appropriate fractions were collected and evaporated to yield 17.5 g (84.0%) of product.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US05597838 |
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| 出典データセット | uspto-grants-1997_01 |
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| ORD ID | ord-6d4e5882a11847748afe36e1a06a6d4e |
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| 出典メモ | uspto-grants-1997_01 |
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