Benzoyl chloride → Ethyl beta-oxo-alpha-phenylbenzenepropanoate

Temperature

0 °C

To 2.5 mL (0.033 mol) of diisopropylamine dissolved in 50 mL of anhydrous tetrahydrofuran at 0° C. under argon was added dropwise 11.1 mL (0.028 mol) of a 2.5 M solution of n-butyllithium in hexanes over 30 min. After the mixture was stirred at 0° C. for 20 min and cooled to −78° C., 2 mL (0.0126 mol) of ethyl phenylacetate was added followed by stirring for 30 min. The resulting solution was treated with 1.61 mL (0.014 mol) of benzoyl chloride at −78° C. After being stirred at −78° C. for 1 h, the reaction mixture was added to 10 mL of saturated NH4Cl solution. The mixture was then diluted with ethyl acetate and washed with saturated NH4Cl solution. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were washed with water (1×) and then with saturated aqueous sodium chloride solution (1×). The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel and eluted with 5-10% ethyl acetate/hexanes to give 1.2 g (36%) of 3-oxo-2,3-diphenylpropionic acid ethyl ester.

1. temperaturecooled to −78° C.
2. stirringby stirring for 30 min
3. stirringAfter being stirred at −78° C. for 1 h
4. washwashed with saturated NH4Cl solution
5. extractionThe aqueous layer was extracted with ethyl acetate
6. washthe combined organic layers were washed with water (1×)
7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe residue was chromatographed on silica gel
11. washeluted with 5-10% ethyl acetate/hexanes

ORD record

ord-777a17d00d034ed595b2552457386af2

Source dataset

uspto-grants-2004_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06673923B2