反应详情

温度

-78 °C

To a solution of 2-bromo-1,5-bis-methoxymethoxy-3-methoxymethyl-benzene (5.66 g, 17.59 mmol) in Et2O (60 mL) was added n-BuLi (15.47 mL, 2.5 M in Hexane) at −78° C. After stirring for 1 hour at −78° C., DMF (13.6 mL, 175.8 mmol) was the added and reaction mixture was allowed to warm to room temperature over 3 hours. The reaction was quenched with saturated NH4Cl and extracted with Et2O. The organic extracts were dried and concentrated in vacuo. The residue was purified by silica gel flash column chromatography to give 2,4-bis-methoxymethoxy-6-methoxymethyl-benzaldehyde (3.93 g, 82%). 1H NMR (400 MHz, CDCl3δ 10.50 (s, 1H), 7.03 (s, 1H), 6.77 (s, 1H), 5.30 (s, 2H), 5.27 (s, 2H), 4.80 (s, 3H), 3.50 (s, 3H), 4.49 (s, 3H).

1. additionadded
2. customreaction mixture
3. temperatureto warm to room temperature over 3 hours
4. customThe reaction was quenched with saturated NH4Cl
5. extractionextracted with Et2O
6. customThe organic extracts were dried
7. concentrationconcentrated in vacuo
8. customThe residue was purified by silica gel flash column chromatography