HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Water → 5-(1,3-Dioxan-2-yl)-1-methyl-1H-imidazole
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Water | HCID 962 | — |
| Edukt | 1,3-Propanediol | HCID 10442 | — |
| Edukt | 1-methyl-1H-imidazole-5-carbaldehyde | HCID 573592 | — |
| Katalysator | Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- | HCID 18462 | — |
| Lösungsmittel | Toluene | HCID 1140 | — |
| Lösungsmittel | Dichloromethane | HCID 6344 | — |
| Produkt | 5-(1,3-Dioxan-2-yl)-1-methyl-1H-imidazole | HCID 57919632 | 57,2% |
Reaktionsschritte
To a solution of 1-methyl-1H-imidazole-5-carbaldehyde (2.9 g, 26.3 mmol) in toluene (20 mL) was added propane-1,3-diol (4.01 g, 52.7 mmol) and CSA (0.306 g, 1.317 mmol) and the reaction mixture was heated to reflux with azeotropic removal of the evolved water for 24 hours. The reaction mixture was cooled to RT, diluted with DCM and washed with NaHCO3 solution. It was then dried over Na2SO4, filtered and concentrated. Purification by column chromatography (80% EtOAc in Hexane to EtOAc) afforded 38 (2.53 g, 57% yield) as a yellow oil which solidified on standing to a yellow solid. MS (m/z): 169.2 (M+H).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08389541B2 |
| Quelldatensatz | uspto-grants-2013_03 |
| ORD ID | ord-8e30ab27481542f4b149006d25c476bc |
| Quellennotiz | uspto-grants-2013_03 |