Hydrochloric Acid → 3-Methyl-5-oxohexanoic acid

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−).

1. temperatureAfter this time, the mixture was cooled to 0° C.
2. additiontreated with ice cold water
3. stirringAfter stirring for 10 min at 0° C.
4. extractionThe acidified mixture was extracted three times with ethyl acetate
5. washthe combined organic layers were washed with saturated aqueous sodium chloride
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated under vacuum

ORD record

ord-5257895491bd4f64937889c0c03c8705

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08507559B2