関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Triethylamine | HCID 8471 | — |
| 反応物 | Trimethylsilylacetylene | HCID 66111 | — |
| 反応物 | Benzoic acid, 2-iodo-, methyl ester | HCID 69132 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 生成物 | Methyl 2-((trimethylsilyl)ethynyl)benzoate | HCID 11053512 | 85.1% |
反応手順
To a solution of 2-iodo-benzoic acid methyl ester (792 mg, 3.02 mmol) in DMF (10 mL) are added trimethylsilylacetylene (854 μL, 6.04 mmol) and triethylamine (2.95 mL, 21.1 mmol). The reaction mixture is degassed for 20 minutes with a stream of nitrogen. Dichloro(bistriphenylphosphene) palladium (II) (212 mg, 0.302 mmol, 10 mol %) and copper (I) iodide (58 mg, 0.302 mmol, 10 mol %) are added and the reaction is heated to 80° C. After 3 h, the reaction is concentrated and the residue is chromatographed eluting with 0 to 5% EtOAc/Hexanes to yield the title compound (597 mg, 85%). GC/MS: 232.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US08106077B2 |
|---|
| 出典データセット | uspto-grants-2012_01 |
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| ORD ID | ord-b3cb5dace8cb4b3cb449666ab2002aaa |
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| 出典メモ | uspto-grants-2012_01 |
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