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Sodium hydride → 2-(alpha-Cyano-4-fluorobenzyl)-5-methylpyridine
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Sodium hydride | HCID 24758 | — |
| 反応物 | Benzeneacetonitrile, 4-fluoro- | HCID 68016 | — |
| 反応物 | 2-Bromo-5-methylpyridine | HCID 564216 | — |
| 反応物 | Sodium p-toluenesulfinate | HCID 2723791 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | 2-(alpha-Cyano-4-fluorobenzyl)-5-methylpyridine | HCID 11413483 | 66.1% |
反応手順
Under argon atmosphere, to a mixture of 4-fluorophenylacetonitrile (3.97 g), 2-bromo-5-methylpyridine (5.00 g) and sodium 4-methylphenylsulfinate (10.48 g) in THF (125 ml) was added sodium hydride (2.35 g, 60%) at 0° C. and the mixture was heated to reflux for 6 hours. The reaction mixture was added to water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate and concentrated under reduced pressure, and the obtained residue was separated and purified by column chromatography (ethyl acetate:hexane 1:4), to give 2-(α-cyano-4-fluorobenzyl)-5-methylpyridine (4.35 g) as yellow oil.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07262185B2 |
| 出典データセット | uspto-grants-2007_08 |
| ORD ID | ord-206ec365cf874c788894c440c4d0cf99 |
| 出典メモ | uspto-grants-2007_08 |