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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 1942767Erstellt: 26. Oktober 2026

Water → 5-(1,3-Dioxan-2-yl)-1-methyl-1H-imidazole

https://huagongshe.com/reaction/1942767

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktWaterHCID 962—
Edukt1,3-PropanediolHCID 10442—
Edukt1-methyl-1H-imidazole-5-carbaldehydeHCID 573592—
KatalysatorBicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 18462—
LösungsmittelTolueneHCID 1140—
LösungsmittelDichloromethaneHCID 6344—
Produkt5-(1,3-Dioxan-2-yl)-1-methyl-1H-imidazoleHCID 5791963257,2%

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

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS08389541B2
Quelldatensatzuspto-grants-2013_03
ORD IDord-8e30ab27481542f4b149006d25c476bc
Quellennotizuspto-grants-2013_03