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1,2-Dichloroethane → (+/-)-trans-3-bromo-6-cyano-3,4-dihydro-2,2-dimethyl-4-[(S)-(-)-3-acetylthio-2-methylpropionyloxy]-2H-1-benzopyran
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | 1,2-Dichloroethane | HCID 11 | — |
| 反応物 | trans-2,2-Dimethyl-3-bromo-6-cyanochroman-4-ol | HCID 6932483 | — |
| 反応物 | S-(3-Chloro-2-methyl-3-oxopropyl) (S)-ethanethioate | HCID 10954137 | — |
| 溶媒 | Pyridine | HCID 1049 | — |
| 生成物 | (+/-)-trans-3-bromo-6-cyano-3,4-dihydro-2,2-dimethyl-4-[(S)-(-)-3-acetylthio-2-methylpropionyloxy]-2H-1-benzopyran | HCID 86745230 | 98.4% |
反応手順
To a mixture of 94 g of (±)-trans-3-bromo-6-cyano-3,4-dihydro-2,2-dimethyl-4-hydroxy-2H-1-benzopyran, 800 ml of ethylene chloride and 32.4 ml of pyridine was added 66 g of (S)-(-)-3-acetylthio-2-methylpropionyl chloride under ice-cooling over 5 minutes and stirred for 1.5 hours under room temperature. The reaction mixture was washed with diluted hydrochloric acid once and 10% aqueous sodium chloride solution twice. The organic layer was separated, dried over magnesium sulfate and concentrated under reduced pressure to give 139.8 g of (±)-trans-3-bromo-6-cyano-3,4-dihydro-2,2-dimethyl-4-[(S)-(-)-3-acetylthio-2-methylpropionyloxy]-2H-1-benzopyran as a light yellow oily substance.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US05162553 |
| 出典データセット | uspto-grants-1992_11 |
| ORD ID | ord-5ce8f967996c4edc9e5c322a720cee3e |
| 出典メモ | uspto-grants-1992_11 |