HCID 86653783, compound → HCID 67159766, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 4-(2,5-bis(benzyloxy)-3,4,6-trimethylphenyl)-N-propylbutanamide (176.6 mg) in TFA (2 mL) was treated with Pd/C (40 mg, 5% Pd by wt), sparged with H2 and heated to 40° C. for 2.25 h. The reaction was cooled, diluted with CH2Cl2, (4 mL) filtered and the solids washed 2×3 mL CH2Cl2 before concentration to a brown oil which solidified upon standing. The crude hydroquinone was dissolved into 1 mL MeCN and 1.5 mL 1 M aqueous CAN added (1.5 mmol, 3.9 equiv.). After 0.25 h, 5 mL EtOAc was added and the organics washed with 4×3 mL saturated NaCl (aq). The combined aqueous layers were back-extracted 2×3 mL EtOAc, the combined organics dried over Na2SO4, concentrated and purified by flash chromatography (gradient elution, 10-50% EtOAc/heptane) yielding N-propyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide as a yellow solid (78.0 mg), MS M++H 278; 1H NMR (400 MHz, CDCl3) δ=5.83 (m, 1 H), 3.24 (q, 2 H), 2.50 (t, 2 H), 2.22 (t, 2 H), 2.08 (s, 3H), 1.97 (s, 6H), 1.71 (pent, 2 H), 1.54 (m, 2 H), 0.92 (t, 3 H) ppm.

Provenance & Evidence