関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Ethanol | HCID 702 | — |
| 反応物 | beta-Bromostyrene | HCID 7667 | — |
| 反応物 | Potassium Carbonate | HCID 11430 | — |
| 反応物 | 1-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | HCID 4912908 | — |
| 触媒 | HCID 178418476 | HCID 178418476 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | 1-methyl-5-(2-phenylethenyl)-1H-pyrazole | HCID 71401987 | 74.5% |
反応手順
Under a nitrogen atmosphere, a mixture of 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.50 g), β-bromostyrene (1.45 g), bis(triphenylphosphine)palladium(II) dichloride (506 mg), potassium carbonate (1.30 g), ethanol (3.8 mL) and dimethylformamide (7.5 mL) was stirred at 75° C. for 6 hours. Thereafter, 13-bromostyrene (1.45 g) was further added to the reaction solution, and the obtained solution was then stirred at 75° C. for 4 hours. Subsequently, the reaction solution was diluted with ethyl acetate, and was then washed with water. The organic layer was dried over anhydrous magnesium sulfate, and was then concentrated under a reduced pressure. The residue was purified by column chromatography (silica gel 60N, hexane:ethyl acetate=4:1 to 3:1), so as to obtain the title compound (990 mg) in the form of a light yellow solid.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 特許番号 | US08642626B2 |
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| 出典データセット | uspto-grants-2014_02 |
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| ORD ID | ord-cdf1f42d84c94674be51e5c49efc0fb6 |
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| 出典メモ | uspto-grants-2014_02 |
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