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1,2-Dimethoxyethane → 2'-(Benzyloxy)-3'-tert-butylbiphenyl-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 Bicarbonate | HCID 516892 | — |
| 反応物 | 3-Formylphenylboronic acid | HCID 2734356 | — |
| 反応物 | 2-(Benzyloxy)-3-tert-butylphenyl trifluoromethanesulfonate | HCID 58238569 | — |
| 触媒 | Dichlorobis(triphenylphosphine)palladium | HCID 6102075 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | 2'-(Benzyloxy)-3'-tert-butylbiphenyl-3-carbaldehyde | HCID 86652859 | 99% |
反応手順
A solution of 8 (3.75 g, 9.65 mmol), 3-formylphenylboronic acid (2.89 g, 19.3 mmol, 2 equiv.), bis(triphenylphosphine) palladium(II) dichloride (0.20 g), glyme (10 mL) and a solution of sodium bicarbonate (2.9 g, 34.5 mmol) in water (50 mL) was stirred well at reflux under nitrogen for 4 hr. After cooling the reaction mixture was diluted with ethyl acetate (150 mL) and washed with water (2×100 mL). The organic layer was dried over sodium sulfate and filtered. The solvent was removed in a rotary evaporator. The crude product was purified by chromatography on silica (120 g) with heptane (3 L) to afford pure 9 (3.19 g, 99%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08541522B2 |
| 出典データセット | uspto-grants-2013_09 |
| ORD ID | ord-f7650247cf4c4e9c8c6415d233b00d00 |
| 出典メモ | uspto-grants-2013_09 |