Nitric Acid → (E)-3-(1,4-Naphthoquinon-2-yl)-2-methylpropenoic acid

Participants

Reaction Steps

Following modified procedures of Shinkawa et al. and Flader et al.16,22 the acid 29a (0.114 g, 0.419 mmol) was dissolved in ethyl acetate (10 mL) at room temperature, then HNO3 (1.0 mL) and AcOH (3 drops) were added at room temperature. The reaction was stirred at room temperature for 4 hours before being diluted with ethyl acetate and washed with brine. The organic layer was dried over MgSO4, filtered, and condensed. The yellow oil was then purified by either flash column chromatography (2:3 Et2O:hexanes 0.5% AcOH) or recrystallization from Et2O/hexanes to afford 30a (0.059 g, 0.24 mmol, 58%) as a yellow solid.

Provenance & Evidence