2(3H)-Furanone, dihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-, (4R)-

2(3H)-Furanone, dihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-, (4R)- Property

Melting point:

78-79 °C

Boiling point:

436.0±18.0 °C(Predicted)

Density 

1.29±0.1 g/cm3(Predicted)

pka

7.02±0.10(Predicted)

Hazard and Precautionary Statements (GHS)

2(3H)-Furanone, dihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-, (4R)- Chemical Properties,Usage,Production

Uses

2(3H)-Furanone, dihydro-4-[(1-methyl-1H-imidazol-5-yl)methyl]-, (4R)- is mainly used in pharmaceutical synthesis and scientific research.

Synthesis

Add aldehyde (0.0320g, 0.2497mmol), potassium carbonate (0.173g, 1.2487 mmol), molecular sieves (3Å), and THF (5mL) to a 15-mL flame-dry round bottom flask equip with a stir bar. Add Methylamine (0.15mL, 0.2997 mmol)、(3R)-Tetrahydro-5-oxo-3-furanacetaldehyde and heat the reaction mixture to 40°C. Complete the reaction after stirring at temperature for 18 h. Filter the reaction mixture to remove molecular sieves upon completion. Concentrate the resulting filtrate in vacuo to half the volume at 25°C follow by addition of 3mL of dichloromethane. Repeat this process three times. Add triethylamine (0.17mL, 1.2487 mmol) and TosMIC (0.1097g, 0.5619 mmol) to the mixture. Stir this reaction at room temperature for 7 days with daily TLC monitoring to track reaction progress. Concentrate the crude mixture to dryness upon completion. Purify by flash chromatography (19:1 DCM:MeOH) to obtain product.

References

[1] CASSANDRA L. SCHRANK . Total synthesis of (+)-pilosinine via a stereodivergent conjugate addition strategy[J]. Tetrahedron Letters, 2020, 61 23: Article 151945. DOI:10.1016/j.tetlet.2020.151945.