Acetic Acid → HCID 78052032, compound

Participants

Reaction Steps

To make a starting compound of Formula I, 11.5 mL of pyrrolidine (0.139 mol, 0.2 eq) and 8.0 mL of acetic acid (0.139 mol, 0.2 eq) were added to a solution of 100 g of ethyl levulinate (0.694 mol, 1.0 eq) in 400 mL of ethanol. To this solution, 76.4 g of 5-methyl-furfural (0.694 mol, 1.0 eq) was added over 30 minutes. The reaction was stirred at ambient temperature until complete, as analyzed by gas chromatography-mass spectrometry (GCMS). The reaction mixture was evaporated to dryness and dissolved in a mixture of 400 mL of hexane and 100 mL of ethyl acetate. Activated charcoal (Darco® G-60, Sigma-Aldrich) was added and stirred for 15 minutes. The reaction mixture was filtered over a six inch sintered glass funnel containing a six inch bed of silica and washed with 4:1 hexane/ethyl acetate to collect 7 fractions. Fractions 3 and 4 were combined and evaporated to an oil to give ethyl 6-(5-methylfuran-2-yl)-4-oxohex-5-enoate as an orange oil (114.6 g, 69.4% yield, proton nuclear magnetic resonance (HNMR), GCMS molecular weight=236).

Provenance & Evidence