2-Trimethylsilyl-4,9-dimethoxy-naphtho[2,3-b]furan → 2-Trimethylsilyl-naphtho[2,3-b]furan-4,9-dione

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Reaction Steps

To 1.2 gram (4 mmoles) of crude product 2-trimethylsilyl-4,9-dimethoxy-naphtho[2,3-b]furan in 50 mL of acetonitrile/water (4:1) in ice bath, 4.8 grams (8.7 mmoles) of cerium ammonium nitrate (CAN) solution in 50 mL of acetonitrile/water (1:4) was added dropwise over 10 minutes. The mixture was further stirred in ice bath for 1 hour, and then evaporated to remove acetonitrile. The remaining aqueous suspension was filtered, and the collected solid was washed with water and crystallized in ethanol/water. Pure crystal product was filtered and dried under vacuum. 0.89 grams of product (overall yield 75%) was obtained and characterized by 1H NMR and mass spectrum. 1H NMR (in CDCl3) δ 0.41 (s, 9H), 7.16 (s, 1H), 7.75-7.78 (m, 2H), 8.19-8.26 (m, 2H). Mass (M+H) is 271.

Provenance & Evidence