Hydrochloric Acid → 3-Methyl-5-oxohexanoic acid

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Reaction Steps

A solution of 5-(methoxy(methyl)amino)-3-methyl-5-oxopentanoic acid (10 mmol) in THF (50 mL) and cooled to −78° C. and treated dropwise with methyllithium (1.4 M in diethyl ether, 2 equivalents). The resulting mixture was warmed to rt where it stirred overnight. After this time, the mixture was cooled to 0° C. and then treated with ice cold water. After stirring for 10 min at 0° C., the mixture was acidified with cold 1 M aqueous HCl. The acidified mixture was extracted three times with ethyl acetate, and the combined organic layers were washed with saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated under vacuum to provide 3-methyl-5-oxohexanoic acid (quantitative yield). Mass spectrum m/z 143.22 (M−H−).

Provenance & Evidence