反应详情

To a solution of (2-(1-methoxycycloheptyl)-5-(trifluoromethyl)phenyl)methanol (167 mg; 0.552 mmol) in methylene chloride (3.0 mL) was added Dess-Martin reagent (290 mg; 0.683 mmol). Reaction was stirred at room temperature for 5 hours. The reaction was diluted with ethyl acetate and quenched with aqueous 1N sodium hydroxide. After partitioning off the aqueous layer, the organic layer was washed with water and brine. It was dried over sodium sulfate and concentrated under reduced pressure. The residue was purified over a Bakerbond 1 g silica cartridge (Mallinkrodt Baker Inc. Phillipsburg, N.J.) (eluted with 0-5% heptane) to yield 167 mg of a cloudy oil. 1H NMR (400 MHz, CDCl3) δ ppm 10.91 (s, 1H), 811 (d, J=2.07 Hz, 1H), 7.73 (dd, J=8.71, 8.30 Hz, 1H), 7.48 (d, J=7.88 Hz, 1H), 2.96 (s, 3H), 2.25 (m, 2H), 2.09 (m, 2H), 1.94-1.57 (m, 8H).

1. customReaction
2. customquenched with aqueous 1N sodium hydroxide
3. customAfter partitioning off the aqueous layer
4. washthe organic layer was washed with water and brine
5. dry with materialIt was dried over sodium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified over a Bakerbond 1 g silica cartridge (Mallinkrodt Baker Inc. Phillipsburg, N.J.) (eluted with 0-5% heptane)
8. customto yield 167 mg of a cloudy oil