Acetic Acid → HCID 71294177, compound

Participants

Reaction Steps

11.3 mL of ethyl levulinate (79.2 mmol) was placed in a ground glass single necked, 24/40, round bottom flask and stirring was begun. This was then chilled with an ice bath. In air, the pyrrolidine (1.25 mL, 15.8 mmol) and acetic acid (0.91 mL, 15.8 mmol) was then added. Hydroxymethyl furfural (HMF) (10.01 g, 79.2 mmol) was then added and solution darkened. The cooling bath was then removed and the solution was stirred at ambient temperature until the reaction was complete (by 1H and 13C NMR). The reaction was then purified by silica gel chromatography (using an ethyl acetate/hexane gradient). 17.1 g of product was obtained (85%). δH(CDCl3) 1.21 (t, J=7 Hz, 3H), 2.60 (t, J=6.6 Hz, 2H), 2.86 (t, J=6.6 Hz, 2H), 4.09 (q, J=7 Hz, 2H), 4.56 (s, 2H), 6.19 (m, 1H), 6.56 (m, 2H), 7.25 (m, 1H). δ13C (CDCl3) 197.6, 172.6, 157.1, 150.0, 128.6, 120.0, 116.7, 109.8, 60.3, 56.8, 35.1, 27.8, 13.6.

Provenance & Evidence