関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Sulfuric Acid | HCID 1118 | — |
| 反応物 | Ethyl orthoformate | HCID 31214 | — |
| 反応物 | 2-Isopropyl-5-methylcyclohexane-1,3-dione | HCID 11988138 | — |
| 反応物 | Cymorcin | HCID 23345336 | — |
| 反応物 | 4-Amino-2-isopropyl-5-methyl-benzene-1,3-diol | HCID 59598754 | — |
| 触媒 | Diamminetetrachlorotitanate(IV) | HCID 160960 | — |
| 溶媒 | Methanol | HCID 887 | — |
| 生成物 | 7-Isopropyl-2,4-dimethyl-benzooxazol-6-ol | HCID 59598632 | — |
反応手順
To a flask charged with 4-amino-2-isopropyl-5-methyl-benzene-1,3-diol (250 mg, 1.4 mmol) (Treibs and Albrecht, “The dihydroxycymenes. IV. Isocymorcin (3,5-dihydroxycymene) from 3,5-menthanedione by dehydrogenation and total synthesis,” Journal fuer Praktische Chemie (1961), 13, 291-305), purged with argon, and cooled to 0° C., was sequentially added triethylorthoformate (0.53 mL, 4.2 mmol), MeOH (2.5 mL), and a 10% v/v solution of H2SO4 in MeOH (25 μL). The reaction was allowed to warm to room temperature slowly, stirred overnight, quenched with saturated NaHCO3, and concentrated. The residue was partitioned between water and methylene chloride. The combined organic phases were dried with Na2SO4 and concentrated. Purification via flash chromatography afforded 175 mg of 7-isopropyl-2,4-dimethyl-benzooxazol-6-ol.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 特許番号 | US08524725B2 |
|---|
| 出典データセット | uspto-grants-2013_09 |
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| ORD ID | ord-f48841bbb421402992e308f5406e6763 |
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| 出典メモ | uspto-grants-2013_09 |
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