関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Hexane | HCID 8058 | — |
| 反応物 | Trimethyl borate | HCID 8470 | — |
| 反応物 | 3-Bromofuran | HCID 89164 | — |
| 反応物 | 7-Methyl-2-oxo-2H-chromen-4-YL trifluoromethanesulfonate | HCID 23370238 | — |
| 反応物 | Butyllithium | HCID 178418339 | — |
| 触媒 | HCID 178418397 | HCID 178418397 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Diethyl Ether | HCID 3283 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 生成物 | 4-(3-Furyl)-7-methylcoumarin | HCID 23370190 | 75.7% |
反応手順
To a solution of 3-bromofuran (2.3 g, 16.1 mmol) in dry Et2O (146 ml) was added at -78° C. n-BuLi in hexane (6.42 ml, 16.1 mmol, 2.5M). The resulting solution was stirred for 20 min, then (MeO)3B (1.82 ml, 16.1 mmol) was added dropwise and after 20 min., a mixture of the triflate from Step 1 (4.50 g, 14.6 mmol) and (PPh3)4Pd (1.69 g, 1.46 mmol) in THF (60 ml) and H2O (10 ml) was added. The cooling bath was removed and the resulting mixture was heated to 65° C. for 1.75 h. The solvent was evaporated and H2O was added followed by extraction with EtOAc (3×50 ml). The combined organic phases were washed with brine, dried over MgSO4 and evaporated. Purification by flash chromatography (toluene:(2-10% EtOAc)) gave 2.5 g of the title compound, m.p. 160°-162° C.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US05424320 |
|---|
| 出典データセット | uspto-grants-1995_06 |
|---|
| ORD ID | ord-e8506f15126a449896a0839e0d8b9da3 |
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| 出典メモ | uspto-grants-1995_06 |
|---|
