Acetate → HCID 44223459, compound

Participants

Reaction Conditions

Reaction Steps

Crude 4-(2,5-dimethoxy-3,4,6-trimethylphenyl)-N-(2-hydroxyethyl)butanamide (1.105 g, 3.57 mmol) was taken up into 40 mL MeCN and 2 mL H2O and cooled to 0° C. To this was added CAN (4.35 g, 7.86 mmol, 2.2 equiv) in 5 mL H2O dropwise over 5 minutes. The reaction was stirred for 0.25 h until judged complete by HPLC and 50 mL ipropyl acetate was added. The organic layer was washed 4×5 mL saturated aqueous NaCl, dried over aqueous Na2SO4 and concentrated to a yellow powder. Flash chromatography (gradient elution 80-100% EtOAc/heptane) yielded 619 mg of N-(2-hydroxyethyl)-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide as a yellow powder. M++H=280 m/z; 1H NMR (400 MHz, CDCl3) δ=6.38 (s, 1 H), 3.77 (t, 2 H), 3.47 (m, 2 H), 2.54 (t, 2 H), 2.29 (t, 2 H), 2.05 (s, 3 H), 2.01 (s, 6 H), 1.76 (m, 2 H+H2O) ppm.

Provenance & Evidence