1-Bromo-3-methylbutane → 4-Methyl-1-{6-[4-(trifluoromethyl)phenyl]-2-pyridinyl}-1-pentanol

참여 물질

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반응 단계

A solution of 6-[4-(trifluoromethyl)phenyl]-2-pyridinecarbaldehyde (350 mg, 1.39 mmol) in Et2O (14 mL) was cooled to 0° C. To this was slowly added the freshly prepared Grignard reagent (1.26 mL, 1.53 mmol), prepared from magnesium turnings (500 mg, 0.02 mol) and 1-bromo-3-methyl butane (2.34 mL, 0.02 mol) in dry Et2O (16.5 mL). The resulting mixture was stirred under nitrogen at 0° C. After 1.5 hours, more Grignard reagent (0.3 mL, 0.36 mmol) was added and the resulting mixture stirred at 0° C. for a further 1.5 hours. The reaction mixture was then quenched by cautious addition of aqueous HCl (2M, 3 mL) and the solvent removed under vacuum. The residue was partitioned between EtOAc (30 mL) and water (20 mL), the layers separated and the aqueous re-extracted with EtOAc (30 mL). The combined organic layer was washed with brine (50 mL), dried (MgSO4) and reduced under vacuum. Purification by SPE (silica, 20 g cartridge), eluting with cyclohexane:EtOAc (gradient 99:1 to 1:1) followed by EtOAc then MeOH afforded the title compound as a colourless oil (179 mg).

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