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Acetyl chloride → 2-Methyl-benzooxazole-4-carboxylic acid ethyl ester
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Acetyl chloride | HCID 6367 | — |
| 反応物 | Triethylamine | HCID 8471 | — |
| 反応物 | Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) | HCID 466102 | — |
| 反応物 | Ethyl 2-amino-3-hydroxybenzoate | HCID 14167647 | — |
| 溶媒 | O-Xylene | HCID 7237 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | 2-Methyl-benzooxazole-4-carboxylic acid ethyl ester | HCID 59316840 | — |
反応手順
A mixture of 2-amino-3-hydroxy-benzoic acid ethyl ester (5.52 mmol; J. Reisch, G. M. K. B. Gunaherath Monatshefte für Chemie, 1988, 119, 1169-1178), acetyl chloride (6.07 mmol), NEt3 (6.07 mmo) and pyridinium p-toluenesulfonate (1.47 mmol) in xylene (60 mL) is heated at reflux for 16 h, cooled to rt, diluted with EtOAc and washed with water. The organic layer is dried over MgSO4 and concentrated in vacuo to give a crude product which is purified by flash chromatography (gradient: heptane to heptane/EtOAc 6/4). LC-MS: tR=0.81 min; [M+H]+=206.0.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08236801B2 |
| 出典データセット | uspto-grants-2012_08 |
| ORD ID | ord-9c140c3a7bd94a99b0ac4d9bdce1a0ac |
| 出典メモ | uspto-grants-2012_08 |