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1-Chloromethylnaphthalene → 4-methoxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 1-Chloromethylnaphthalene | HCID 6845 | — |
| 反応物 | Sodium hydride | HCID 24758 | — |
| 反応物 | 4-methoxy-2-methyl-1H-indole | HCID 10773274 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Dimethylformamide | HCID 6228 | — |
| 生成物 | 4-methoxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole | HCID 10638039 | 97.1% |
反応手順
4-Methoxy-2-methyl-1H-indole (644 mg, 4 mmol) was dissolved in 10 mL of DMF and 160 mg (4 mmol) of 60% NaH/mineral oil was added. After 0.67 hours, 707 mg (4 mmol) of 1-(chloromethyl)naphthalene was added. After 5 hours, the mixture was diluted with water and extracted twice with ethyl acetate. The combined ethyl acetate was washed with brine, dried (MgSO4) and concentrated at reduced pressure. The residue was chromatographed on silica gel and eluted with 20% EtOAc/hexane to give 1.17 g (97% yield) of 4-methoxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US05733923 |
| 出典データセット | uspto-grants-1998_03 |
| ORD ID | ord-80c7b751a3284a8b966f0ea7134ae600 |
| 出典メモ | uspto-grants-1998_03 |