Hydrochloric Acid → 1-[5-Benzyloxy-4-methoxy-2-(5-methyl-[1,2,4]oxadiazol-3-yl)phenyl]-2-methylpropan-1-ol

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Reaction Steps

A mixture of 3-(4-benzyloxy-2-iodo-5-methoxy-phenyl)-5-methyl-[1,2,4]oxadiazole (reference example 4-1) (844 mg) and tetrahydrofuran (6 mL) was cooled in an ice salt bath under an argon atmosphere. Isopropylmagnesium chloride (2.0 mol/L tetrahydrofuran solution, 1.2 mL) was added, and the mixture was stirred under ice-salt-bath cooling for 10 minutes. After an addition of isobutyraldehyde (0.55 mL), the mixture was stirred in an ice salt bath for 10 minutes, and at room temperature for 30 minutes. Water and 2 mol/L hydrochloric acid were added to the mixture, and the mixture was extracted with ethyl acetate. The separated organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 15%-35% ethyl acetate/hexane, gradient elution) to give the title compound (533 mg).

Provenance & Evidence