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1-Chloro-4-(chloromethyl)benzene → 1-[(4-chlorophenyl)methyl]-2-methyl-5-methoxy-1H-indole-3-acetic acid ethyl ester
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 1-Chloro-4-(chloromethyl)benzene | HCID 7723 | — |
| 反応物 | Sodium hydride | HCID 24758 | — |
| 反応物 | 1-(4-Chlorobenzyl)-5-methoxy-2-methylindole-3-acetic acid | HCID 4059895 | — |
| 反応物 | Ethyl (5-methoxy-2-methyl-1H-indol-3-yl)acetate | HCID 10729163 | — |
| 生成物 | 1-[(4-chlorophenyl)methyl]-2-methyl-5-methoxy-1H-indole-3-acetic acid ethyl ester | HCID 10523286 | — |
反応手順
1-[(4-Chlorophenyl)methyl]-5-methoxy-2-methyl-1H-indole-3-acetic acid. The procedure in Example 63, Part B, was used to react 1.35 g (5.5 mmol) of 5-methoxy-2-methyl-1H-indole-3-acetic acid ethyl ester with 240 mg (6 mmol) of 60% NaH/mineral oil and 970 mg (6 mmol) of p-chlorobenzyl chloride to give 1.4 g of 1-[(4-chlorophenyl)methyl]-2-methyl-5-methoxy-1H-indole-3-acetic acid ethyl ester that had been chromatographed on silica (20% ether/hexane→35% ether/hexane). This ester was hydrolyzed with 3 mL of 5N NaOH to give 1.23 g of crude 1-[(4-chlorophenyl)methyl]-5-methoxy-2-methyl-1H-indole-3-acetic acid.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US05578634 |
| 出典データセット | uspto-grants-1996_11 |
| ORD ID | ord-4e4fdb465f8e449dae485fea100ecccb |
| 出典メモ | uspto-grants-1996_11 |