2-Iodoxybenzoic acid → HCID 59456512, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ortho-iodoxybenzoic acid (1.56 g, 5.57 mmol) in dimethyl sulfoxide (17 ml), (E,4aR,8aR)-8-(bromomethylene)-octahydro-4a-methylnaphthalene-2(1H)-one (Compound 25: 955 mg, 3.71 mmol) was added, and the resulting mixture was stirred at 80° C. for 18 hours. The resulting mixture was cooled to room temperature, and 5% aqueous sodium hydrogen carbonate solution was added thereto. The resulting mixture was extracted with diethyl ether, and the organic layer was washed with water and saturated brine. Further, the combined aqueous layer was extracted with ethyl acetate which was then washed with water and saturated brine. The combined organic layer was dried over sodium sulfate and evaporated under reduced pressure. The obtained crude product (976 mg) was purified by flash column chromatography to obtain (4aR,8E,8aR)-8-(bromomethylene)-4a,5,6,7,8,8a-hexahydro-4a-methylnaphthalene-2(1H)-one (443 mg, 46.8%). 1H NMR (CDCl3) δ: 6.76 (d, J=9.9 Hz, 1H), 5.88 (d, J=9.9 Hz, 1H), 5.74 (t, J=1.5 Hz, 1H), 2.95-3.10 (m, 1H), 2.66 (ddd, J=11.7 Hz, 5.7 Hz, 1.5 Hz, 1H), 2.45 (d, J=12.0 Hz, 1H), 2.43 (d, J=6 Hz, 1H), 1.50-1.90 (m, 5H), 0.98 (s, 3H)

Provenance & Evidence