関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Trimethylsilylacetylene | HCID 66111 | — |
| 反応物 | Methyl 4-iodobenzoate | HCID 69273 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 触媒 | HCID 178418397 | HCID 178418397 | — |
| 溶媒 | Toluene | HCID 1140 | — |
| 生成物 | Methyl 4-ethynylbenzoate | HCID 640163 | 147.4% |
反応手順
To a solution of methyl 4-iodobenzoate (1.5 g, 5.72 mmol) and trimethylsilylacetylene (Aldrich, 1.58 mL, 11.45 mmol) in toluene (12 mL) were added Pd(PPh3)4 (0.66 g, 0.57 mmol), CuI (0.16 g, 0.86 mmol), and TEA (6.4 mL, 45.80 mmol). The resulting reaction mixture was purged with nitrogen for 3 min and stirred at rt for 3 h. The reaction mixture was diluted with ethyl acetate and NH4Cl solution. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography (eluting with 10% EtOAc/hexane) to afford the title compound as a white solid (1.35 g, 96%). 1H NMR (CDCl3) δ 7.98 (d, J=8.6 Hz, 2H), 7.53 (d, J=8.6 Hz, 2H), 3.92 (s, 3H), 0.27 (s, 9H); MS(ESI+) m/z 233.1 (M+H)+.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US09345740B2 |
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| 出典データセット | uspto-grants-2016_05 |
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| ORD ID | ord-fd6cd99dcff044b0b717c51cc4dd5ec7 |
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| 出典メモ | uspto-grants-2016_05 |
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