Diethyl Ether → alpha-Methyl-4-(3-pyridylmethyl)benzyl alcohol

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Reaction Steps

Under an atmosphere of nitrogen, 1.5 ml of a 3 M solution of methylmagnesium iodide in diethyl ether were added to a solution of 830 mg of the aldehyde (prepared as described in Reference Example 1) in 20 ml of tetrahydrofuran at -70° C., the mixture was allowed to warm from -70° C. to room temperature over a period of one hour with stirring, poured into a saturated aqueous solution of ammonium chloride, and extracted with diethyl ether. The extract was washed with water, and a saturated aqueous solution of sodium chloride, dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (1:1) as eluent to give 547 mg of the title compound having the following physical characteristics:

Provenance & Evidence