関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | 3-Furaldehyde | HCID 10351 | — |
| 反応物 | Triphenylphosphine Oxide | HCID 13097 | — |
| 反応物 | Phosphonium | HCID 5460504 | — |
| 反応物 | Potassium tert-butoxide | HCID 23665647 | — |
| 反応物 | Methyl 2-(3-benzyl-2-thienyl)-3-methoxypropenoate | HCID 54504656 | — |
| 反応物 | Methyl 3-methoxy-2-(3-phenoxymethyl-2-thienyl)propenoate | HCID 54572621 | — |
| 触媒 | Benzyltriphenylphosphonium chloride | HCID 70671 | — |
| 溶媒 | Water | HCID 962 | — |
| 溶媒 | Diethyl Ether | HCID 3283 | — |
| 生成物 | (E)-3-styrylfuran | HCID 14326174 | 32.1% |
反応手順
Potassium tert-butoxide (35.7 g) was added in one portion to a stirred suspension of benzyltriphenylphosphonium chloride (41.6 g) in ether (1 liter). After 1 hour, a solution of 3-formylfuran (17.5 g) in ether (60 ml) was added to the resulting orange mixture which was then stirred for 2 hours, poured into water, and extracted with ether. The extracts were washed with water, dried and concentrated to give a solid. Trituration of this solid with ether enabled much of the weakly-soluble triphenylphosphine oxide and excess phosphonium salt to be separated, and the ether-soluble fraction (37.06 g) was chromatographed using ether as eluent to give a mixture of (E)- and (Z)-isomers of 3-styrylfuran (27 g) as a yellow solid. Crystallisation twice from methanol gave (E)-3-styrylfuran (5.12 g), mp 96° C., as a yellow solid.
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US05258360 |
|---|
| 出典データセット | uspto-grants-1993_11 |
|---|
| ORD ID | ord-9f272b85516241a9987d72e581965f9a |
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| 出典メモ | uspto-grants-1993_11 |
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