Phthalic Anhydride → HCID 86590097, compound

Participants

Reaction Steps

Phthalic anhydride (566 mg, 3.82 mmol) was dissolved in acetonitrile (10 mL) and treated with urea-hydrogen peroxide complex (360 mg, 3.82 mmol) and the suspension was stirred for 15 min. A portion of the Boc-derivative from stage (i) (890 mg, 3.48 mmol) was added and the suspension was stirred at room temperature for 20 h. The residue was partitioned between potassium carbonate solution (100 mL) and DCM (200 mL). The organic layer was separated and the aqueous layer was re-extracted with DCM (3×50 mL). The combined organic fractions were washed with brine, dried (MgSO4) and evaporated to an oil. Purification by flash chromatography [SiO2; DCM/MeOH/880 NH3 (90:10:1)] afforded the title compound (680 mg, 72%); δH (CDCl3, 300 MHz) 1.42 (9H, s), 2.91 (3H, s), 4.44 (2H, s), 7.23 (1H, d), 8.00 (1H, d), 8.08 (1H, s); MS m/z (TS+) 273 (MH+).

Provenance & Evidence