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Water → (2R,6R)-2-(2'-phenylethyl)-6-methyl-1,3-dioxan-4-one
関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|---|---|---|
| 反応物 | Water | HCID 962 | — |
| 反応物 | Benzenepropanal | HCID 7707 | — |
| 反応物 | 3-Hydroxybutanoic acid, (R)- | HCID 92135 | — |
| 反応物 | Pyridinium.p-toluenesulfonate | HCID 22033616 | — |
| 溶媒 | Dichloromethane | HCID 6344 | — |
| 生成物 | (2R,6R)-2-(2'-phenylethyl)-6-methyl-1,3-dioxan-4-one | HCID 13741776 | 63.5% |
反応手順
A mixture of (R)-3-hydroxybutanoic acid (7.8 g), 3-phenylpropionaldehyde (6.71 g) and pyridinium toluene-4-sulphonic acid (ca. 10 mmol %) in dichloromethane (300 ml) was stirred, under reflux, for 48 hours with removal of water. The reaction mixture was cooled to room temperature, washed three times with saturated sodium bicarbonate, dried (MgSO4) and evaporated under reduced pressure. The residue was crystallised from ether/pentane to give (2R,6R)-2-(2'-phenylethyl)-6-methyl-1,3-dioxan-4-one (7.0 g), m.p. 49.7°-50.9° C.; [α]DR.T. =15.2(c=1.05; CHCl3).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| 特許番号 | US04812476 |
| 出典データセット | uspto-grants-1989_03 |
| ORD ID | ord-22f3e655f0634123b861e7ded464c1aa |
| 出典メモ | uspto-grants-1989_03 |