Aluminium lithium hydride → (5-Fluoro-2-(pent-4-en-2-yloxy)phenyl)methanol

Participants

Reaction Steps

To a solution of methyl 5-fluoro-2-(pent-4-en-2-yloxy)benzoate (1.00 g, 4.20 mmol) in THF (10 mL) cooled to 0° C. was added dropwise lithium aluminum hydride (5.04 ml, 5.04 mmol) over 30 min. The resulting mixture was stirred at rt for 2 h. The reaction was diluted with 2 mL THF and cooled to 0° C. and quenched by the dropwise addition of brine. The mixture was further diluted with 5 mL EtOAc and the organic phase was decanted off, dried (Na2SO4), filtered and concentrated to give (5-fluoro-2-(pent-4-en-2-yloxy)phenyl)methanol (0.80 g, 3.81 mmol, 91% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.04 (dd, J=8.7, 3.1 Hz, 1H), 6.93 (td, J=8.5, 3.1 Hz, 1H), 6.82 (dd, J=8.9, 4.3 Hz, 1H), 5.86 (ddt, J=17.1, 10.1, 7.1 Hz, 1H), 5.25-5.06 (m, 2H), 4.75-4.54 (m, 2H), 4.54-4.38 (m, 1H), 2.51 (dt, J=13.9, 6.7 Hz, 2H), 1.42-1.31 (m, 3H).

Provenance & Evidence