Tetrahydrofuran → 3-(4-Fluorophenyl)propan-1-ol

Participants

Reaction Conditions

Reaction Steps

A mixture of 2.5 g (15 mmol) of 4-fluorocinnamic acid and 0.06 g of (PPh3)3RhCl (Wilkinson's catalyst) in 5 mL of Et3SiH was heated at 100° C. for 3 h. The reaction mixture was cooled to rt, and to it was added 20 mL of THF and 30 mL (30 mmol) of LiAlH4 (1 M in THF) and the reaction mixture was stirred at 40° C. for 3 h. The reaction mixture was cooled to rt and to it was successively added 3 mL of H2O, 3 mL of 15% KOH solution and 3 mL of H2O. The reaction mixture was filtered and the Al-salts were washed with ethyl acetate. The combined organic fraction was dried over MgSO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, hexanes: ethyl acetate, 4:1) to give 2.26 g of the title compound.

Provenance & Evidence