4-(4-fluorophenyl)butan-1-ol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following the process described in example 18 (point A), starting from 4-hydroxybenzaldehyde and 4-(4-fluorophenyl)-1-butanol, the title compound was prepared (43% yield).

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of aluminium trichloride (10.2 g, 76.5 mmol) in dichloromethane (250 ml) at 0° C. was added with the borane-tert-butylamine complex (13.2 g, 153 mmol) and the mixture was left under stirring at 0° C. for 15 minutes. After that the mixture was added with 3-(4-fluorobenzoyl)propionic acid (5 g, 25.5 mmol) stirring at room temperature for 20 h, then added slowly with 0.2M HCl (75 ml) and extracted with ethyl acetate (3×100 ml). The combined organic phases were washed with 0.2M HCl and with a NaCl saturated solution, dried and the solvents were removed under reduced pressure. The resulting residue was purified by chromatography through a silica gel column, eluting with hexane:ethyl acetate, 8:2, thereby recovering 2.70 g of the title product as a colourless oil (63% yield). was added with the borane-tert-butylamine complex (13.2 g, 153 mmol) the mixture was left stirring at room temperature for 20 h extracted with ethyl acetate (3×100 ml) The combined organic phases were washed with 0.2M HCl and with a NaCl saturated solution dried the solvents were removed under reduced pressure The resulting residue was purified by chromatography through a silica gel column eluting with hexane