[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([O:9][CH3:10])[C:3]=1[CH2:11][C:12](O)=[O:13].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([O:9][CH3:10])[C:3]=1[CH2:11][CH2:12][OH:13]To a solution of 2-(2,3-difluoro-6-methoxyphenyl)acetic acid (1 g, 4.95 mmol) in THF (20 mL) at 0° C. was added 1M LAH (9.89 mL, 9.89 mmol) in THF and the resulting mixture was heated at 60° C. for 3 h. Mixture was then cooled and quenched with dropwise addition of water (0.5 mL), 1N NaOH (0.5 mL), and then 1 mL H2O. After stirring for 15 min, the mixture was filtered through celite. The filtrate was concentrated in vacuo. The residue was dried under high vacuum to afford 2-(2,3-difluoro-6-methoxyphenyl)ethanol (810 mg, 4.30 mmol, 87% yield) as a clear viscous oil. Used as is in the next step without further purification. 1H NMR (500 MHz, CDCl3) δ 7.01 (q, J=9.2 Hz, 1H), 6.62-6.53 (m, 1H), 3.92-3.75 (m, 5H), 3.00 (td, J=6.6, 1.9 Hz, 2H), 1.65 (t, J=5.7 Hz, 1H).
Wird geladen…
