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(Trifluoromethyl)trimethylsilane → ethyl 6-methyl-8-(2,2,2-trifluoro-1-hydroxyethyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | (Trifluoromethyl)trimethylsilane | HCID 552549 | — |
| 反応物 | ethyl 8-formyl-6-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate | HCID 86599485 | — |
| 触媒 | Tetramethylammonium fluoride | HCID 67803 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | ethyl 6-methyl-8-(2,2,2-trifluoro-1-hydroxyethyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylate | HCID 86599487 | 116% |
反応手順
The aldehyde from Example 605a, Step 1 (2.0 g, 6.37 mmol) in THF (20 mL) was cooled to 0° C. and treated with 98% trimethyl(trifluoromethyl)silane (1.18 g, 8.28 mmol) and 15 mg tetramethylammonium fluoride. The reaction was allowed to warm to room temperature and stirred for overnight. The HF (48%, 0.24 mL) was added to the reaction and the reaction was stirred for 6 hours. After LCMS indicated that there was no starting material in the reaction, the reaction was quenched with water, extracted with ethyl acetate, washed with water, brine, dried over MgSO4, and concentrated in vacuo to give a yellow semisolid (2.84 g), which had suitable purity to use without further purification.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07259266B2 |
| 出典データセット | uspto-grants-2007_08 |
| ORD ID | ord-fd1be1d60e2d47369ff2eeafcd3216d2 |
| 出典メモ | uspto-grants-2007_08 |