Acetic Anhydride → HCID 59516072, compound

Participants

Reaction Conditions

Reaction Steps

t-Butyl cyanoacetate (3.525 g, 25 mmol) was dissolved in triethyl orthoformate (6.2 mL, 37.5 mmol). Acetic anhydride (2.41 mL, 25 mmol) was added and the mixture heated to 125° C. for 3 h. Volatiles were then removed by evaporation under reduced pressure to leave an orange oil. The crude oil was dissolved in methanol and methyl 2-(4-hydrazinylphenyl)acetate hydrochloride (Intermediate #39) (1.62 g, 7.5 mmol) and DIPEA (1.3 mL, 7.5 mmol) were added. The mixture was heated to reflux for 2 h and then evaporated to dryness. The residue was dissolved in ethyl acetate (100 mL), washed with water (2×50 mL) and brine (50 mL), dried (MgSO4) and evaporated to leave a crude to product which was purified by flash chromatography on silica gel (elution gradient 0-50% EtOAc in isohexane) to give the title compound as a yellow solid. (974 mg, 39%)

Provenance & Evidence