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Acetic Acid → 2,2-Difluoroethenyl 4-methylbenzene-1-sulfonate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Acetic Acid | HCID 176 | — |
| 反応物 | Ethyl Acetate | HCID 8857 | — |
| 反応物 | Ethanol, 2,2,2-trifluoro-, 1-(4-methylbenzenesulfonate) | HCID 67942 | — |
| 反応物 | Butyllithium | HCID 178418339 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | 2,2-Difluoroethenyl 4-methylbenzene-1-sulfonate | HCID 10977366 | 47.1% |
反応手順
Add n-butyllithium (1.6 M in hexanes, 4.9 mL, 7.8 mmol) dropwise over 5 min to a solution of 2,2,2-trifluoroethyl-p-toluene sulfonate (1.0 g, 3.9 mmol) in THF (20 mL) at −78° C. Stir for 30 min, add acetic acid (225 μL, 3.9 mmol) and stir for 30 min. Warm to room temperature, add ethyl acetate and extract with saturated aqueous ammonium chloride, and saturated aqueous sodium bicarbonate. Dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 0:100 to 15:85 ethyl acetate:hexanes) to give the title compound as an oil (430 mg, 47%).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07618978B2 |
| 出典データセット | uspto-grants-2009_11 |
| ORD ID | ord-5260bac620324b1db61f7ceea865017a |
| 出典メモ | uspto-grants-2009_11 |