Isobutyryl chloride → Ethyl 2-(4-hexylphenyl)-4-methyl-3-oxopentanoate

Temperature

-60 °C

6.0 g (24 mmol) of ethyl 2-(4-hexylphenyl)acetate was dissolved in 130 mL of dry tetrahydrofuran under a nitrogen atmosphere and cooled to −60° C. After addition of 31.8 mL (36.2 mmol) of 1.14 M solution of lithiumdiisopropylamine in hexane/tetrahydrofuran, the solution was warmed to 0° C. and stirred for 1 hours. The reactuion solution was cooled to −60° C. again and stirred with 3.6 g (34 mmol) of isobutyryl chloride at −60° C. to room temperature for 15 hours. The reaction was quenched with saturated aqueous sodium hydrogen carbonate (150 ml), and the reaction solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate:hexane (0:100 to 1:9) as the eluent to give 5.39 g of the desired product as a pale yellw oil.

1. temperaturethe solution was warmed to 0° C.
2. temperatureThe reactuion solution was cooled to −60° C. again
3. customThe reaction was quenched with saturated aqueous sodium hydrogen carbonate (150 ml)
4. extractionthe reaction solution was extracted with ethyl acetate
5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationthe filtrate was concentrated under reduced pressure
8. customThe resulting residue was purified by silica gel column chromatography

ORD record

ord-6240f5aad3754305a4564a1319224a31

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08658686B2