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Hydrochloric Acid → (3S,8S,9S,10R,13S,14S,16S,17R)-17-[(1R,5R)-6-hydroxy-1,5-dimethyl-hexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,16-diol
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Hydrochloric Acid | HCID 313 | — |
| 反応物 | Diosgenin | HCID 99474 | — |
| 触媒 | Zinc | HCID 23994 | — |
| 溶媒 | Ethanol | HCID 702 | — |
| 生成物 | (3S,8S,9S,10R,13S,14S,16S,17R)-17-[(1R,5R)-6-hydroxy-1,5-dimethyl-hexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,16-diol | HCID 11729441 | 85% |
反応手順
To a 5-liter flask were sequentially added diosgenin (40 grams, 0.0965 moles, zinc dust (900 grams, -325 mesh size) and 2 liters of absolute ethanol. The suspension was then brought to reflux and 800 ml of concentrated HCl was added dropwise over a period of 2.5 hours. The reaction was refluxed for an additional 30 minutes then immediately filtered while hot, under gravity, over Whatman no. 2 filter paper to remove the zinc particles. Two liters of water was then added to the filtrate and a white precipitate formed. The mixture was cooled at room temperature and the precipitate was collected by suction filtration (Whatman no. 2 paper) and washed three times with water, then air dried to afford 35 grams (85% yield) of compound (2).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US05274088 |
| 出典データセット | uspto-grants-1993_12 |
| ORD ID | ord-b6fa099e9e494e258320e8eb3527737e |
| 出典メモ | uspto-grants-1993_12 |