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

Temperature

100 °C

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.

1. temperatureThe reaction mixture was cooled to rt
2. temperatureThe reaction mixture was cooled to rt and to it
3. filtrationThe reaction mixture was filtered
4. washthe Al-salts were washed with ethyl acetate
5. dry with materialThe combined organic fraction was dried over MgSO4
6. filtrationfiltered
7. concentrationthe filtrate was concentrated
8. customThe residue was purified by chromatography (silica, hexanes: ethyl acetate, 4:1)

ORD record

ord-2c532713e063447b82dbbc8367b1e7e7

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06303593B1