Aluminium lithium hydride → (S)-(4,5-difluoro-2-(pent-4-en-2-yloxy)phenyl)methanol

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Reaction Steps

To a solution of (S)-4,5-difluoro-2-(pent-4-en-2-yloxy)benzaldehyde (0.1295 g, 0.572 mmol) in THF (2 ml) at 0° C. was added dropwise lithium aluminum hydride (0.343 ml, 0.687 mmol) over 30 min. The mixture was stirred at rt for 2 h then cooled to 0° C. and quenched by the dropwise addition of brine. The mixture was partitioned between EtOAc and water. The organic phase was washed with brine, dried (Na2SO4), filtered and concentrated to give (S)-(4,5-difluoro-2-(pent-4-en-2-yloxy)phenyl)methanol (0.1088 g, 0.477 mmol, 83% yield) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.15 (dd, J=10.4, 9.2 Hz, 1H), 6.72 (dd, J=12.0, 6.6 Hz, 1H), 5.99-5.70 (m, 1H), 5.24-5.07 (m, 2H), 4.75-4.49 (m, 2H), 4.41 (sxt, J=6.0 Hz, 1H), 2.60-2.35 (m, 2H), 2.26 (t, J=6.5 Hz, 1H), 1.36 (d, J=6.1 Hz, 3H).

Provenance & Evidence