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A solution of 6-[4-(trifluoromethyl)phenyl]-2-pyridinecarbaldehyde (300 mg, 1.19 mmol) in dry toluene (12 mL) under nitrogen was cooled to 0° C. (ice/water bath) and treated with n-pentylmagnesium bromide (0.66 mL of a 2M solution in Et2O, 1.31 mmol) and the resulting mixture was stirred at 0° C. for 2 hours. The reaction was then quenched by the cautious addition of aqueous HCl (2M, 2 mL) and the solvent was removed under vacuum and the residue partitioned between EtOAc (2×50 mL) and aqueous HCl (2M, 50 mL). The organic solution was washed with water (60 mL) then brine (60 mL), dried (MgSO4) and reduced. Purification by SPE (silica, 20 g cartridge) eluting with cyclohexane:EtOAc (gradient 99:1 to 19:1) afforded the title compound as a colourless oil (131 mg).

1. customThe reaction was then quenched by the cautious addition of aqueous HCl (2M, 2 mL)
2. customthe solvent was removed under vacuum
3. customthe residue partitioned between EtOAc (2×50 mL) and aqueous HCl (2M, 50 mL)
4. washThe organic solution was washed with water (60 mL)
5. dry with materialbrine (60 mL), dried (MgSO4)
6. customPurification by SPE (silica, 20 g cartridge)
7. washeluting with cyclohexane