3-Oxetanone

[6704-31-0] C3H4O2 (MW 72.06) InChI = 1S/C3H4O2/c4-3-1-5-2-3/h1-2H2 InChIKey = ROADCYAOHVSOLQ-UHFFFAOYSA-N (used for the synthesis of advanced oxetane and other heterocyclic building blocks) 1-3 Alternate Name: 1,3-epoxy-2-propanone. Physical Data: density: 1.124 g mL−1 at 25 °C; flash point 26 °C. Form Supplied in: liquid (colorless to yellow to brown). Analysis of Reagent Purity: 1H NMR4; 13C NMR4; IR absorption frequency: 1802–1820 cm−1 (CO), ∼900 cm−1 (ring).3 Preparative Method: treatment of oxetan-3-ol with P2O5, DMSO, and Et3N at −5 °C provided the 3-oxetanone in 48% yield after distillation without aqueous workup.2 Alternatively, 3-oxetanone can also be synthesized following a four-step sequence with 23% overall yield. The synthetic route began with the conversion of dihydroxyacetone into its dimethylacetal. Then monotosylation of the isolated 1,3-dihydroxy-2,2-dimethoxypropane and subsequent ring closure with NaH furnished 2,2-dimethoxyoxetane. Finally, acidic cleavage of the ketal in presence of Montmorillonite K10 at reflux provided the desired 3-oxetanone after purification by distillation.1, 5 Other processes that can also be employed for the synthesis of 3-oxetanone include the oxidative cleavage of 3-methyleneoxetanones with osmium tetroxide and sodium periodate3 and gold-catalyzed intermolecular oxidation of propargylic alcohol.6 Purification: distillation at 50–56 °C /91 mbar; to avoid exothermic decomposition, the operation should be performed at below 80 °C.4 Handling, Storage, and Precautions: the reagent is potentially hazardous and is recommended to be stored in a closed container under −20 °C. The reagent is harmful by inhalation, in contact with skin, and if swallowed. The reagent should be protected from heat, flames, spark, and oxidizing agents. The possible hazardous combustion product of the reagent is carbon monoxide. The reagent is unstable in the presence of base and slowly polymerizes on standing, giving a highly viscous material, possibly polyoxetanone [CH2C(O)CH2O].7