Water → 2,6-Heptanedione

N,O-Dimethylhydroxylamine hydrochloride (42 g, 431 mmol) was added to a dichloromethane (500 ml) solution of glutaryl chloride (25 ml, 196 mmol) at room temperature, and pyridine (95 ml, 1.18 mol) was dropped under ice-cooled condition. After being stirred at room temperature for 2 hours, the reaction mixture was celite filtered. The filtrate was concentrated under reduced pressure, and diethyl ether (300 ml) was added. The mixture was celite filtered again, and concentrated under reduced pressure to give a Weinreb diamide product. The Weinreb diamide product was dissolved in tetrahydrofuran (500 ml), and a 3 M diethyl ether solution (160 ml, 0.470 mol) methylmagnesium bromide was slowly dropped under ice-cooled condition. After being stirred at room temperature for 4 hours, the mixture was brought back to ice-cooled condition, and water was slowly added. After extraction with ethyl acetate, the reaction liquid was washed with saturated brine. The organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was then purified by silica gel column chromatography to give heptane-2,6-dione (20.3 g, 81%).

1. temperaturecooled condition
2. additionwas slowly added
3. extractionAfter extraction with ethyl acetate
4. customthe reaction liquid
5. washwas washed with saturated brine
6. dry with materialThe organic layer was dried over magnesium sulfate
7. customthe solvent was evaporated under reduced pressure
8. customThe residue was then purified by silica gel column chromatography

ORD record

ord-b7d654bfa02844b7b8945e2c5d2714a0

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09114390B2