関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Diethyl Ether | HCID 3283 | — |
| 反応物 | Dimethylformamide | HCID 6228 | — |
| 反応物 | 5-Bromo-2-(4-fluoro-benzyloxy)-pyridine | HCID 59255502 | — |
| 反応物 | Butyllithium | HCID 178418339 | — |
| 溶媒 | Water | HCID 962 | — |
| 生成物 | 6-(4-Fluoro-benzyloxy)-pyridine-3-carbaldehyde | HCID 59255111 | 72.5% |
反応手順
To a diethyl ether (150 mL) solution of 5-bromo-2-(4-fluoro-benzyloxy)-pyridine (3.75 g 13.3 mmol) described in Manufacturing Example 58-1-1 was added n-butyl lithium (2.55 M n-hexane solution, 6.26 mL, 16.0 mmol) on a dry ice-ethanol bath (−78° C.) under nitrogen atmosphere, which was stirred for 30 minutes at −78° C. N,N-dimethylformamide (1.54 mL, 20.0 mmol) was then added dropwise and stirred for 5 minutes at −78° C. The reaction solution was allowed to room temperature, water was added, and the solution was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:heptane=1:3) to obtain the title compound (2.23 g, 72.5%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 特許番号 | US08841327B2 |
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| 出典データセット | uspto-grants-2014_09 |
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| ORD ID | ord-21a50570643f405dac5799be6d8831db |
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| 出典メモ | uspto-grants-2014_09 |
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