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Lithium Chloride → 5-Methoxy-2-methyl-benzofuran-7-carboxylic acid methyl ester
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Lithium Chloride | HCID 433294 | — |
| 反応物 | 3-Allyl-2-hydroxy-5-methoxy-benzoic acid methyl ester | HCID 14838669 | — |
| 触媒 | Cupric acetate | HCID 8895 | — |
| 触媒 | Palladium Chloride | HCID 24290 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 生成物 | 5-Methoxy-2-methyl-benzofuran-7-carboxylic acid methyl ester | HCID 59560465 | 100.9% |
反応手順
To a solution of 3-allyl-2-hydroxy-5-methoxy-benzoic acid methyl ester (4b) (1.48 g, 6.66 mmol) in DMF (30 mL) was added Cu(OAc)2 (3.63 g, 19.98 mmol), LiCl (847 mg, 19.98 mmol) in H2O (1 mL) and PdCl2 (24 mg, 0.133 mmol). The reaction mixture was stirred at RT for 3 h, quenched with H2O (100 mL) and NH4OH (5 mL) and extracted with EtOAc (100 mL). The organic layer was washed with H2O (100 mL), dried over MgSO4 and concentrated. The residue was purified by flash column chromatograph eluting with 10-15% EtOAc/hexane to give colorless oil (1.48 g, 48%). 1H NMR (400 MHz, CDCl3) δ 7.43 (d, J=2.53 Hz, 1 H) 7.17 (d, J=2.53 Hz, 1 H) 6.36 (s, 1 H) 4.00 (s, 3 H) 3.87 (s, 3 H) 2.51 (s, 3 H)
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US08119624B2 |
| 出典データセット | uspto-grants-2012_02 |
| ORD ID | ord-acc340d7a3a844cf94629aad272434ef |
| 出典メモ | uspto-grants-2012_02 |