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Ethylene Glycol → 3-Hydroxy-5beta-estran-17-one ethylene ketal
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Ethylene Glycol | HCID 174 | — |
| 反応物 | Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) | HCID 466102 | — |
| 反応物 | Ethyl acetate hexane | HCID 21226206 | — |
| 反応物 | 3-Hydroxy-5betaestran-17-one | HCID 22795659 | — |
| 溶媒 | Benzene | HCID 241 | — |
| 溶媒 | Ethyl Acetate | HCID 8857 | — |
| 生成物 | 3-Hydroxy-5beta-estran-17-one ethylene ketal | HCID 86760179 | 94.8% |
反応手順
Compound 4(10 g, 36.2 mmol) was dissolved in dry benzene (150 ml) mixed with ethylene glycol (25 ml, 280 mmol) and pyridinium p-toluenesulfonate (1 g, 3.9 mmol) and refluxed using a Dean-stark separator overnight till no starting material was detected by TLC. The cold solution was diluted with EtOAc (100 ml), washed twice with brine, dried on Na2SO4 and the solvents removed under reduced pressure. Flash-chromatography on silica gel with EtOAc: Hexane 4:6 as eluant to give 11.0 g (94.5% yield) the title compound as a white solid.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US07087590B2 |
| 出典データセット | uspto-grants-2006_08 |
| ORD ID | ord-faa2f348d6f5478eb5c5bd468fd5e72f |
| 出典メモ | uspto-grants-2006_08 |