関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Diethylamine | HCID 8021 | — |
| 反応物 | Trimethylsilylacetylene | HCID 66111 | — |
| 反応物 | Tetrabutylammonium Fluoride | HCID 2724141 | — |
| 反応物 | (2-Phenyl4bromobenzoyl)-methionine methyl ester | HCID 20622824 | — |
| 触媒 | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| 触媒 | Palladium(2+) acetate--triphenylphosphane (1/2/2) | HCID 84538 | — |
| 溶媒 | Toluene | HCID 1140 | — |
| 溶媒 | Diethyl Ether | HCID 3283 | — |
| 生成物 | (4-Ethynyl-2-phenylbenzoyl)methionine methyl ester | HCID 54338681 | — |
反応手順
A mixture of (2-phenyl-4-bromobenzoyl)-methionine methyl ester (100 mmol), diethylamine (300 mmol), trimethylsilylacetylene (110 mmol), bis(triphenylphosphine) palladium diacetate (5 mmol) and copper(I) iodide (3 mmol) in toluene is heated at 60° C. until TLC analysis indicates the starting methyl ester has disappeared. The reaction mixture is concentrated in vacuo, redissolved in ether, filtered through silica gel, and concentrated. The residue is then dissolved in THF, and is treated with tetrabutylammonium fluoride (120 mmol). After TLC analysis indicates that no starting material is left, the reaction mixture is diluted with ether, washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue is then purified with column chromatography on silica gel to give the title product.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US06221865B1 |
|---|
| 出典データセット | uspto-grants-2001_04 |
|---|
| ORD ID | ord-b1295a32a5004ca08bcd2230412b11eb |
|---|
| 出典メモ | uspto-grants-2001_04 |
|---|
