Triethyl orthoacetate → HCID 68710756, compound

Participants

Reaction Steps

Ethyl 2-Hydroxyimino-3-oxobutanoate (1.67 g, 10.5 mmol) (Example C), 3-trifluoromethyl-4-methoxyaniline (2.0 g, 10.5 mmol) and pyridinium p-toluenesulfonate (0.13 g, 0.52 mmol) were stirred at 75° C. in toluene (15 ml) for 4 hrs. The reaction mixture was evaporated under vacuum at 40° C. The residue was dissolved in triethyl orthoacetate (14.3 ml, 78 mmol) and p-toluenesulfonic acid monohydrate (0.1 g, 0.52 mmol), and palladium on charcoal (0.6 g) were added. The reaction mixture was stirred for 4 hrs under hydrogen atmosphere. The dark suspension was filtered and evaporated to dryness. The crude product was recrystallized at 0° C. from TBME and n-heptane. The desired product was obtained as a light brown solid (1.28 g, 36%), MS: m/e=343.1 (M+H+).

Provenance & Evidence