Diethyl Succinate → HCID 178471162, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-methyl-1H-pyrazole-4-carbaldehyde (9 g, 82 mmol) and diethyl succinate (57 g, 327 mmol) in t-butanol (50 mL), a solution of t-BuOK (37.3 g, 245 mmol) in t-butanol (40 mL) was added and the mixture was heated to 80° C. for 4 hours. The mixture was concentrated; the obtained residue was dissolved in water (50 mL), acidified (pH˜2) using 6 N HCl and extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with aqueous NaHCO3 (2×50 mL). The combined aqueous layers were acidified (pH˜2) and extracted with ethyl acetate (2×100 mL). The combined ethyl acetate layers were washed with saturated aqueous NaCl (25 mL), dried over anhydrous Na2SO4 and concentrated to afford 3-(ethoxycarbonyl)-4-(3-methyl-1H-pyrazol-4-yl)but-3-enoic acid (20 g, 100%) as gum. 1H NMR (CDCl3) δ 7.85 (s, 1H), 7.65 (s, 1H), 4.3 (t, 2H), 3.65 (s, 2H), 4.4 (s, 3H), 1.3 (t, 3H).

Provenance & Evidence