反应详情

温度

-78 °C

n-Butyllithium 2.5M in hexanes (5.6 mL) was added slowly to a solution of 5-methoxybenzofuran (13.5 mmol) in dry THF (30 mL) at −78° C. After 1 h stirring at −78° C., triisopropylborate (27.0 mmol) was added dropwise and the mixture was stirred for another 20 min at −78° C. The dry ice bath was removed and HCl 2N (aq. 40 mL) was added and the mixture allowed to warm to r.t. and then poured in water (50 mL). The resulting aqueous solution was extracted with ether, the organic layer was washed with brine, dried over MgSO4, filtered and concentrated under vacuum to afford the title compound as a beige powder (2.40 g). 1H NMR δ ppm 8.49 (s, 2 H) 7.45 (d, 1 H) 7.38 (s, 1 H) 7.18 (d, 1 H) 6.93 (dd, 1 H) 3.78 (s, 3 H).

1. stirringthe mixture was stirred for another 20 min at −78° C
2. customThe dry ice bath was removed
3. additionHCl 2N (aq. 40 mL) was added
4. temperatureto warm to r.t.
5. additionpoured in water (50 mL)
6. extractionThe resulting aqueous solution was extracted with ether
7. washthe organic layer was washed with brine
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated under vacuum