Sodium Bicarbonate → (Rac.) 4-(4-chloro-3-fluoro-2-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanal

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Reaction Steps

1.00 g (2.59 mmol) of (rac.) 4-(4-chloro-3-fluoro-2-methoxyphenyl)-4-methyl-2-(trifluoromethyl)-2-hydroxy-pentanoic acid ethyl ester is dissolved in 9.5 ml of diethyl ether and mixed in portions with 73.7 mg (1.94 mmol) of LiAlH4 at 0° C. Stirring is continued at 0° C. and a TLC is drawn off every one-quarter hour. After forty minutes of stirring at 0° C., the reaction mixture is mixed drop by drop with 2.4 ml of saturated NaHCO3 solution while being cooled in an ice bath. It is vigorously stirred for 30 minutes while being cooled in an ice bath and overnight at room temperature. The precipitate is suctioned off, washed with ethyl acetate, and the filtrate is concentrated by evaporation in a rotary evaporator. After chromatography of the residue on a Flashmaster, 560.2 mg is obtained. This is a 3:2 mixture of the aldehyde with the starting ester.

Provenance & Evidence