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1,2-Dimethoxyethane → 5-(3,5-Dimethylisoxazol-4-yl)-2-methylfuran-3-carbaldehyde
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 1,2-Dimethoxyethane | HCID 8071 | — |
| 反応物 | Sodium Carbonate | HCID 10340 | — |
| 反応物 | 3,5-Dimethylisoxazole-4-boronic acid | HCID 2734346 | — |
| 反応物 | 5-Bromo-2-methylfuran-3-carbaldehyde | HCID 46941673 | — |
| 触媒 | HCID 178418397 | HCID 178418397 | — |
| 溶媒 | Water | HCID 962 | — |
| 生成物 | 5-(3,5-Dimethylisoxazol-4-yl)-2-methylfuran-3-carbaldehyde | HCID 86646384 | 69% |
反応手順
A mixture of 5-bromo-2-methylfuran-3-carbaldehyde (1.9 g), 3,5-dimethylisoxazole-4-boronic acid (1.7 g), tetrakis(triphenylphosphine)palladium(0) (0.6 g), 2N aqueous sodium carbonate solution (9 mL) and 1,2-dimethoxyethane (20 mL) was stirred overnight with refluxing under an argon atmosphere. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (0% ethyl acetate/hexane to 30% ethyl acetate/hexane), and crystallized from ethyl acetate/hexane to give the title compound (1.4 g, 69%) as a yellow crystal.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08309580B2 |
| 出典データセット | uspto-grants-2012_11 |
| ORD ID | ord-6f5ae90eceec4027b83d9dccf571bd95 |
| 出典メモ | uspto-grants-2012_11 |