Acetone → HCID 54168845, compound

To acetone (30 ml) were added 4-bromobutyric acid ethyl ester (1.5 ml, 10.5 mmol) and potassium thioacetate (1.8 g, 15.8 mmol), and the mixture was stirred at room temperature for 30 minutes and then filtered, and the solids were washed with acetone. The filtrate was concentrated, and then purified by column chromatography on silica gel (hexane:ethyl acetate=5:1) to give 4-acetylthiobutyric acid ethyl ester (2.03 g). Then, ethyl magnesium bromide (1.04M solution in tetrahydrofuran, 31.3 ml, 32.6 mmol) in dry tetrahydrofuran (8 ml) was cooled to 0° C. under an argon atmosphere, and a solution of 886 mg of the compound obtained as above in dry tetrahydrofuran (4 ml) was added dropwise and the mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with an aqueous saturated ammonium chloride solution, acidified with 10% hydrochloric acid and extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=4:1) to give the title compound (221 mg, 2 steps, 29%).

1. filtrationfiltered
2. washthe solids were washed with acetone
3. concentrationThe filtrate was concentrated
4. custompurified by column chromatography on silica gel (hexane:ethyl acetate=5:1)

ORD record

ord-6e851bcd406348b6a20000bb6b3d3e4d

Source dataset

uspto-grants-1998_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05824811