Nitrogen → 5-Methylsulfanylfuran-2-carboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of commercially available 5-nitro-furan-2-carboxylic acid ethyl ester (5.00 g, 27.01 mmol) in DMSO (34.5 mL) was treated at rt with sodium methanethiolate (2.05 g 27.82 mmol). The mixture was then stirred overnight at 100° C., treated at rt with sat. aq. NH4Cl (250 mL) and the aqueous layer was extracted with EA (3×100 mL). The combined org. extracts were washed with sat. aq. NaHCO3 (100 mL) and brine (100 mL), dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (70:30 hept-EA) gave the title compound: TLC:rf (70:30 hept-EA)=0.52. LC-MS-conditions 02: tR=0.96 min; [M+AcCN+N+H]+=228.23.

Provenance & Evidence