HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
2-Butene-1,4-diol → (Z)-4-(Tetrahydro-2H-pyran-2-yl-oxy)but-2-en-1-ol
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | 2-Butene-1,4-diol | HCID 8065 | — |
| Edukt | 3,4-dihydro-2H-pyran | HCID 8080 | — |
| Edukt | Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) | HCID 466102 | — |
| Lösungsmittel | Tetrahydrofurane dichloromethane | HCID 21919333 | — |
| Produkt | (Z)-4-(Tetrahydro-2H-pyran-2-yl-oxy)but-2-en-1-ol | HCID 10975949 | 481,9% |
Reaktionsbedingungen
| Temperatur | 0 °C |
|---|
Reaktionsschritte
Dihydropyran (9.1 ml, 100 mmol) was added dropwise to a cooled (0° C.) solution of 2-butene-1,4-diol (8.8 g, 10 mmol) and pyridinium paratoluenesulfonate (0.25 g, 10 mmol) in anhydrous dichloromethane:tetrahydrofuran (2:1). The mixture was stirred two days at 0° C. then concentrated in vacuo. The residue was purified by flash chromatography on silica gel (ethyl acetate:hexane 3:7) to give 8.3 g of the title compound (49%).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US05416076 |
| Quelldatensatz | uspto-grants-1995_05 |
| ORD ID | ord-0deb034b167b441282245b88540d7147 |
| Quellennotiz | uspto-grants-1995_05 |