Triethylamine → HCID 15521919, compound

Participants

Reaction Steps

To a stirred solution of levulinic acid (30 g, 0.258 mol) in CHCl3 (850 mL) at 0° C. was added triethylamine (43.2 mL, 0.310 mol), followed by isobutyl chloroformate (37 mL, 0.284 mol) over 15 minutes. After 30 minutes, triethylamine (57.6 mL, 0.413 mol) was added, followed by N,O-dimethylhydroxylamine hydrochloride (37.8 g, 0.387 mol) in 5 portions over 5 minutes. Vigorous bubbling ensued, and the mixture was allowed to warm to RT and stirred for 1 h. The mixture was reduced to a moist solid by rotary evaporation under reduced pressure, slurried in 500 mL EtOAc, washed with 10% K2CO3, brine, and dried over Na2SO4. Evaporative removal of the solvent gave 2-1 as a yellow oil. TLC Rf =0.42 (silica,1:1 chloroform/ethyl acetate). 1H MM (300 MHz, CDCl3) δ 3.74 (s, 3H), 3.18 (s, 3H), 2.65-2.95 (m, 4H), 2.21 (s, 3H).

Provenance & Evidence