Ethyl Acetate → HCID 19710589, compound

Participants

Reaction Steps

To a vigorously stirred solution of NaIO4 (1.69 g, 7.89 mmol, Baker) in water (50 mL), there was added a solution of 1,2,3,4-tetrahydro-6-methoxy-1,4-methanonaphthalene-5,8-diol (52, 543 mg, 2.63 mmol) in CHCl3 (20 mL). The vigorously stirred reaction immediately became orange. The reaction was allowed to stir for 15 min at rt at which point TLC analysis (10% EtOAc, 90% CHCl3) showed the total consumption of the organic starting material and the formation of a yellow, higher Rf spot. The layers were separated and the aqueous portion extracted with CHCl3 (2×20 mL). The combined organic portion was washed with half saturated brine (30 mL), filtered through cotton and the solvent removed in vacuo. The residue was filtered through a plug of silica gel with CHCl3 elution. Solvent removal gave 53 as a yellow semisolid. Scraping this semisolid with a spatula resulted in a yellow powder. This was further dried in vacuo (470 mg, 88%, pure by TLC and 1H NMR); mp 106°-108° C.; 1H NMR (CDCl3) δ1.16 (m, 2H), 1.40 (d, J=9.0 Hz, 1H), 1.63 (d, J=8.7 Hz, 1H), 1.91 (m, 2H), 3.50 (m, 2H), 3.78 (s, 3H), 5.72 (s, 1H).

Provenance & Evidence