関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Boron trifluoride etherate | HCID 8000 | — |
| 反応物 | 2-Methyl-3-nitrophenol | HCID 79579 | — |
| 反応物 | Sodium Bicarbonate | HCID 516892 | — |
| 反応物 | Tert-butyl 2,2,2-trichloroethanimidate | HCID 2734700 | — |
| 溶媒 | Tetrahydrofuran | HCID 8028 | — |
| 溶媒 | Cyclohexane | HCID 8078 | — |
| 生成物 | 2-Methyl-1-[(2-methyl-2-propanyl)oxy]-3-nitrobenzene | HCID 45097160 | — |
反応手順
To a solution of 2-methyl-3-nitrophenol K1 (1.1 g; 7.18 mmol) in THF (13 mL) was added cyclohexane (27 mL; a solution was maintained). tert-Butyl trichloroacetimidate K2 (5.36 mL; 28.73 mmol) was added followed by a catalytic amount of boron trifluoride etherate (143.8 μL; 1.14 mmol) and the reaction was stirred at room temperature for 15 h. The reaction was incomplete (by analytical HPLC) and an additional amount of tert-butyl trichloroacetimidate (1.4 mL; 7.51 mmol) was added (reaction remains in solution). The reaction was complete after stirring at room temperature for 5 h. Solid sodium bicarbonate was added, and the mixture was filtered, rinsed with dichloromethane and evaporated to dryness to provide a white solid. The solid was triturated with dichloromethane, the white solid filtered and discarded (=trichloroacetimide). The filtrate was concentrated and loaded onto a flash column for purification (hexane:EtOAc 9:1) to provide the pure 2-methyl-3-tert-butoxynitrobenzene K3 (1.17 g; 78%). Homogeneity by HPLC (TFA) @ 220 nm: 96%
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 特許番号 | US07939667B2 |
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| 出典データセット | uspto-grants-2011_05 |
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| ORD ID | ord-d5561b44fd274d4aa2b41fb3a2c0fba5 |
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| 出典メモ | uspto-grants-2011_05 |
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