反应详情

温度

-78 °C

To 4-bromo-2-isopropylanisole (3) (12 g, 52.4 mmol) in 300 mL of tetrahydrofuran at -78° C. was added 68 mL of tert-Butyllithium (1.7M in pentane). The reaction mixture was stirred for 10 min at -78° C. and then 2,6-dimethyl-4-methoxybenzaldehyde (6) (8.6 g, 52.4 mmol) was added. The reaction mixture was stirred for 1 hour at -78° C. and for 1.5 hours at room temperature, diluted with 150 mL of ether, washed with 150 mL of water, acidified with 1N HCl, and washed with 5×50 mL of brine. The organic portion was dried (MgSO4), filtered, and evaporated to give the crude product, which was purified by flash column chromatography (silica gel, 95:5 hexane/ethylacetate) to yield 3,5-dimethyl-4-(3'-isopropyl-4'-methoxybenzylhydroxy) anisole (7) (12 g, 38.2 mmol, 73%) as an oil; 1HNMR (CDC13) δ 1.2 (dd, 6H), 2.27 (s, 6H), 3.30 (heptet, 1H), 3.80 (s, 6H), 6.26 (s, 1H), 6.59 (s, 2H) 6.76 (d, 1H), 6.89 (d, 1H), 7.24 (s, 1H).

1. stirringThe reaction mixture was stirred for 1 hour at -78° C. and for 1.5 hours at room temperature
2. washwashed with 150 mL of water
3. washwashed with 5×50 mL of brine
4. dry with materialThe organic portion was dried (MgSO4)
5. filtrationfiltered
6. customevaporated
7. customto give the crude product, which
8. customwas purified by flash column chromatography (silica gel, 95:5 hexane/ethylacetate)