Veratrole → 1-(2,3-Dimethoxyphenyl)-4-chlorobutan-1-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of TMEDA (6.6 mmol) in dry THF (15 mL), was added Sec-BuLi (6.6 mmol) slowly at −78° C. The reaction mixture was stirred at −78° C. for 10 minute, veratrole (6.0 mmol) in THF (3 mL) was added slowly. The reaction was stirred at −78° C. for 30 minutes, 1-chlorobutan-4-al (6.6 mmol) was added and stirred at −78° C. for 2 hr. The reaction mixture was warmed to rt, added brine (1 mL), and filtered. The filtrate was dried over MgSO4, filtered and concentrated to a residue. The residue was purified by flash column chromatography (Silica gel; Ethyl acetate/Hexane: 3/7) to afford 1-(2,3-dimethoxyphenyl)-4-chlorobutan-1-ol in 20% yield. 1H NMR (300 MHz, CDCl3) δ7.05 (dd, J=8.0 Hz, 7.7 Hz, 1H), 6.94 (bd, J=7.7 Hz, 1H), 6.85 (bd, J=8.1 Hz, 1H), 4.91-4.97 (m, 1H), 3.88 (s, 3H), 3.84 (s, 3H), 3.56-3.60 (m, 2H), 2.44-2.45 (m, 1H), 1.81-2.00 (m, 4H) ppm. MS (CI, NH3) m/e 244 (base, M+H+).

Provenance & Evidence