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Sodium Carbonate → 5-(2,2,2-Trifluoro-1,1-dimethyl-ethoxy)-pyridine-2-carbonitrile
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Sodium Carbonate | HCID 10340 | — |
| 反応物 | Sodium hydride | HCID 24758 | — |
| 反応物 | 1,1,1-Trifluoro-2-methylpropan-2-ol | HCID 68182 | — |
| 反応物 | 2-Cyano-5-fluoropyridine | HCID 11332453 | — |
| 溶媒 | Hexamethylphosphoramide | HCID 12679 | — |
| 生成物 | 5-(2,2,2-Trifluoro-1,1-dimethyl-ethoxy)-pyridine-2-carbonitrile | HCID 57656626 | 79.4% |
反応手順
Add 2-trifluoromethyl-2-propanol (1.1 g, 8.3 mmol) slowly to a slurry of sodium hydride (202 mg, 60% mineral oil, washed with hexane) in HMPA (3 mL) under nitrogen. Stir the slurry for 15 min, then add 5-fluoro-pyridine-2-carbonitrile (510 mg, 4.2 mmol). Stir the slurry for 16 h at ambient temperature. Adjust the mixture to pH 9 with sodium carbonate then extract with diethyl ether (3×50 mL). Collect the organic layer, dry over Na2SO4 and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (95/5 to 80/20) to obtain the desired intermediate (768 mg, 79%). GC-MS m/z: 230 (Me).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08022062B2 |
| 出典データセット | uspto-grants-2011_09 |
| ORD ID | ord-a77b1277e1ac4efd8e56ec36ce2c3f17 |
| 出典メモ | uspto-grants-2011_09 |