Chloroform → HCID 19710581, compound

Participants

Reaction Steps

To a vigorously stirred solution of NaIO4 (471 mg, 2.20 mmol, Baker) in water (15 mL), there was added solid 1,4-dihydro-6-methoxy-1,4-methanonaphthalene-5,8-diol (48, 150 mg, 734 μmol) in one portion. The reaction immediately became orange and a precipitate formed. The reaction was allowed to stir at rt for 15 min at which point TLC analysis (10% EtOAc, 90% CHCl3) indicated total consumption of 48. The reaction mixture was extracted with CHCl3 (3×15 mL). The extract was washed with half saturated brine (1×25 mL), filtered through cotton and the solvent removed in vacuo to yield a gummy yellow solid. This was triturated with hexanes (2 mL) and dried in vacuo to yield 49 as a yellow powder (134 mg, 90%, pure by TLC and 1H NMR); mp 117°-118° C.; 1H NMR (CDCl3) δ2.26 (d, J=7.2 Hz, 1H), 2.33 (d, J=6.9 Hz, 1H), 3.79 (s, 3H), 4.10 (m, 2H), 5.70 (s, 1H), 6.86 (m, 2H). Note: this material decomposes if stored for extended periods at rt.

Provenance & Evidence