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Triethylamine → 1-(4'-t-Butyldimethylsilyloxy-3'-methoxyphenyl)-1-butene-3-one
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Triethylamine | HCID 8471 | — |
| 反応物 | 4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one | HCID 14121 | — |
| 反応物 | tert-Butyldimethylsilyl chloride | HCID 28928 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | 1-(4'-t-Butyldimethylsilyloxy-3'-methoxyphenyl)-1-butene-3-one | HCID 54529210 | 80.3% |
反応手順
To a methylene chloride (100 mL) solution of 1-(4'-hydroxy-3'-methoxyphenyl)-1-butene-3-one (10.0 g, 52 mmol) is added triethyl amine (5.8 g, 57.2 mmol) and t-butylchlorodimethyl silane (15.7 g, 104 mmol). The reaction is stirred at room temperature for 12 hours under an argon atmosphere. The mixture is washed with water (3×100 mL) and brine (100 mL). The organic layer is dried over MgSO4 and evaporated. Flash chromatography (ethyl ether/hexane 1:1) affords 12.8 g (80%) of the desired 1-(4'-t-butyldimethylsilyloxy-3'-methoxyphenyl)-1-butene-3-one, mp=65°-68° C.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US05208251 |
| 出典データセット | uspto-grants-1993_05 |
| ORD ID | ord-9b54f7bddead4d4aa5b16fd475188053 |
| 出典メモ | uspto-grants-1993_05 |