Hydrochloric Acid → Ethyl 3-(5-chlorothiophen-2-yl)-3-oxopropanoate

To a solution of 5-chlorothiophene-2-carboxylic acid (10.12 g, 62.24 mmol) in tetrahydrofuran (80 ml) was added 1,1′-carbonyldiimidazole (11.1 g, 68.5 mmol) at room temperature and the mixture was stirred as it was for 6 hrs. Monoethyl malonate monomagnesium salt (9.81 g, 34.2 mmol) was added to this mixture at room temperature and the mixture was stirred at 60° C. for 3 hrs. The reaction solution was diluted with ethyl acetate and water, and acidified with conc. hydrochloric acid. The ethyl acetate layer was separated, and the aqueous layer was extracted with ethyl acetate. The collected organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (hexane/ethyl acetate=6/1) to give the objective substance.

1. stirringthe mixture was stirred at 60° C. for 3 hrs
2. customThe ethyl acetate layer was separated
3. extractionthe aqueous layer was extracted with ethyl acetate
4. dry with materialThe collected organic layer was dried over anhydrous sodium sulfate
5. customthe solvent was evaporated under reduced pressure
6. customThe obtained crude product
7. customwas purified by silica gel column chromatography (hexane/ethyl acetate=6/1)
8. customto give the objective substance

ORD record

ord-cb90d1f7c08f4069b88408ba96707fdf

Source dataset

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06982348B2