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Cesium carbonate → Methyl 5-methyl-2-[(2S)-oxiran-2-ylmethoxy]benzoate
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Cesium carbonate | HCID 10796 | — |
| 反応物 | Methyl 5-methylsalicylate | HCID 89802 | — |
| 反応物 | Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl ester | HCID 146490 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 生成物 | Methyl 5-methyl-2-[(2S)-oxiran-2-ylmethoxy]benzoate | HCID 86601490 | 72% |
反応手順
A solution of methyl 2-hydroxy-5-methylbenzoate (0.166 g, 1 mmol), (2S)-oxiran-2-ylmethyl 3-nitrobenzenesulfonate (0.26 g, 1 mmol) and caesium carbonate (0.39 g, 1.2 mmol) in dimethylformamide (5 mL) was stirred at room temperature overnight. The mixture was partitioned between water and ethyl acetate, and the organic phase was washed twice with water and once with brine, and finally concentrated. The crude material was purified by flash chromatoghrphy on silica gel (eluent:ethyl acetate/n-heptane), yielding the titled compound (0.16 g, 72%) as colourless oil.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07449475B2 |
| 出典データセット | uspto-grants-2008_11 |
| ORD ID | ord-004c7494ad88477b9d69d45ca9932e4a |
| 出典メモ | uspto-grants-2008_11 |