関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Dimethylformamide | HCID 6228 | — |
| 反応物 | 5-Bromo-2-phenoxypyridine | HCID 22346845 | — |
| 反応物 | Butyllithium | HCID 178418339 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | 6-Phenoxynicotinaldehyde | HCID 2776500 | 32% |
反応手順
To a solution of 5-bromo-2-phenoxy-pyridine described in Manufacturing Example 231-1-1 (18.7 g, 74.6 mmol) in tetrahydrofuran (360 mL) was added n-butyl lithium (31.1 mL, 2.64 M hexane solution, 82.1 mmol) under nitrogen atmosphere at −78° C., which was stirred for 30 minutes at −78° C. To this reaction solution was added N,N-dimethylformamide (7.46 mL, 97 mmol) at −78° C., which was stirred for 1 hour at this temperature. The reaction solution was partitioned into ethyl acetate and water. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=5:1) to obtain the title compound (4.75 g, 32%).
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-e63b264174214bd89303b46794ad14bb |
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| 出典メモ | uspto-grants-2014_09 |
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