反应详情

To a solution of 3,5-dimethyl-4-(4′-fluoro-3′-iso-propylbenzyl)triisopropylsilanoxybenzene in THF (10 mL) at 0° C. was added TBAF (1 M, 4.0 mL). The reaction mixture was stirred for 3 h, diluted with ethyl acetate 920 mL) and quenched with water (10 mL). The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel, eluting with ethyl acetate-hexanes (1:9) to afford 3,5-dimethyl-4-(4′-fluoro-3′-iso-propylbenzyl)phenol (450 mg, 61% for two steps): 1H NMR (300 MHz, CDCl3): δ 6.97 (d, J=7.4 Hz, 1 H), 6.86 (m, 1 H), 6.69 (m, 1 H), 6.60 (s, 2 H), 3.95 (s, 2 H), 3.20 (m, 1 H), 2.22 (s, 6 H), 1.25 (d, J=6.4 Hz, 6 H). TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=ethyl acetate-hexanes (1:9); Rf=0.50.

1. customquenched with water (10 mL)
2. dry with materialThe organic layer was dried over MgSO4
3. filtrationfiltered
4. concentrationconcentrated under reduced pressure
5. customThe crude product was purified by column chromatography on silica gel
6. washeluting with ethyl acetate-hexanes (1:9)