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Water → Tetrahydrofuran-3-yl 4-methylbenzenesulfonate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Water | HCID 962 | — |
| 反応物 | Pyridine | HCID 1049 | — |
| 反応物 | 4-Toluenesulfonyl chloride | HCID 7397 | — |
| 反応物 | 3-Furanol, tetrahydro- | HCID 9960 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 溶媒 | Ethylacetate heptane | HCID 21899848 | — |
| 生成物 | Tetrahydrofuran-3-yl 4-methylbenzenesulfonate | HCID 13837325 | 67.5% |
反応手順
To a mixture of 3-hydroxytetrahydrofuran (7.00 g, 79.5 mmol) and pyridine (100 mL), was added p-toluenesulfonyl chloride (18.2 g, 95.4 mmol) while stirring at room temperature, and the resulting mixture was stirred for 8.5 hours. To the mixture, were added water and ethyl acetate. After thoroughly shaking the mixture, the organic layer was separated, and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was filtered, and then the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate: n-heptane/ethyl acetate=4/1) to obtain the title compound (13.0 g, 53.7 mmol).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08530504B2 |
| 出典データセット | uspto-grants-2013_09 |
| ORD ID | ord-872bb89e4f994941b3711d549ccabc83 |
| 出典メモ | uspto-grants-2013_09 |