Potassium Hydroxide → 5-(4-Fluorophenyl)pentan-1-ol

Participants

Reaction Conditions

Reaction Steps

Under nitrogen atmosphere, at 0° C., to a stirring mixture of LiAlH4 (0.27 g, 7.1 mmol) in dry Et2O (6 mL), 5-(4′-fluorophenyl)valeric acid (0.35 g, 1.8 mmol) in dry Et2O (5 mL) was added dropwise. The mixture was left to react at room temperature for 4 hrs, then at 0° C. H2O (0.35 mL), 3M KOH solution (0.35 mL) and N2O (1 mL) were very slowly added. The mixture was stirred for 1 hr at 0° C., filtered to remove the solid residue, and the organic phase dried over Na2SO4. The organic solution was again filtered and concentrated to dryness affording the title compound (0.32 g, 97%) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 1.34-1.47 (m, 2H), 1.55-1.72 (m, 4H), 2.49-2.68 (m, 2H), 3.64 (t, J=6.56 Hz, 2H), 6.86-7.03 (m, 2H), 7.06-7.17 (m, 2H).

Provenance & Evidence