Hydrochloric Acid → 1-(3-Cyclopentyloxy-4-methoxyphenyl)-3-methylbutan-1-ol

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Reaction Steps

To a magnetically-stirred solution of 3-cyclopentyloxy-4-methoxybenzaldehyde (25.0 mmol, 5.50 g) of Example 1A, in anhydrous ethyl ether (250 mL) at 0° C. is added isobutylmagnesium chloride (30 mmol, 15 mL; 2.0M solution in ethyl ether) dropwise over 20 minutes. The reaction mixture is allowed to stir while slowly warming to room temperature over 1 hour and is then poured into 1N HCl (250 mL) and partitioned with ethyl ether (200 mL). The aqueous phase is extracted with ethyl ether (200 mL) and the combined organics are washed with aqueous saturated NaHCO3 (200 mL), aqueous saturated NaCl (200 mL), and dried (MgSO4). Concentration in vacuo affords a yellow oil which is purified by flash chromatography (SiO2 : 1) methylene chloride, 2) 2% ethyl acetate/methylene chloride, 3) 5% ethyl acetate/methylene chloride) to give the title compound as a white solid (21.5 mmol, 5.98 g; 86 %).

Provenance & Evidence