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Hydrochloric Acid → (4R)-6-bromo-2-methyl-2-(trifluoromethyl)chroman-4-ol
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Hydrochloric Acid | HCID 313 | — |
| 反応物 | Tetrahydrofuran | HCID 8028 | — |
| 反応物 | (3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo(1,2-c)(1,3,2)oxazaborole | HCID 2734713 | — |
| 反応物 | (Dimethyl sulfide)trihydroboron | HCID 12423031 | — |
| 反応物 | 6-Bromo-2-methyl-2-(trifluoromethyl)chroman-4-one | HCID 67305602 | — |
| 溶媒 | Toluene | HCID 1140 | — |
| 生成物 | (4R)-6-bromo-2-methyl-2-(trifluoromethyl)chroman-4-ol | HCID 67305384 | — |
反応手順
To a cooled (ice bath) solution of (s)-2-methyl-cbs-oxazaborolidine 1.0 M in toluene (100 μl, 100 μmol) was added borane-dimethyl sulfide 2.0 M in THF (500 μl, 1000 μmol). After stirred 15 min, a solution of 6-bromo-2-methyl-2-(trifluoromethyl)chroman-4-one (309 mg, 1000 μmol) in toluene was added drop wise. The reaction was completed after stirring 9h at 0° C. 2N HCl was added slowly to quench the reaction. The resulted mixture was extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel column to afford the title compound.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07745484B2 |
| 出典データセット | uspto-grants-2010_06 |
| ORD ID | ord-9e879ac3aa344099b227c59bf71a01e4 |
| 出典メモ | uspto-grants-2010_06 |