1,2-Dichloroethane → HCID 58573959, compound

To a 500-mL round-bottomed flask was added silica gel 60 (21 g, 350 mmol) and the flask was heated with a heat gun under high vacuum for 30 min. The system was cooled to room temperature and phosphorus pentoxide (8.75 mL, 148 mmol) was added. The mixture was stirred at 110° C. (oil bath) under high vacuum for 120 min. The mixture was allowed to cool to room temperature. 3-chlorophenylacetic acid (15.6 g, 91 mmol), 2-chlorothiophene (33.8 mL, 366 mmol) and DCE (50 mL) were added. The reaction mixture was stirred at reflux for 4 hours. LCMS analysis showed the reaction was complete. The reaction mixture was allowed to cool to room temperature. The reaction mixture was diluted with ether (300 mL) and filtered. The organic solution was concentrated under reduced pressure. The residue was triturated with hexane to afford the title compound as an off-white solid. The hexane mother liquid was concentrated and purified by flash chromatography (SiO2, 0 to 30% EtOAc/Hex, a gradient elution) provided another batch of the title compound as a light yellow solid. Mass Spectrum (ESI) m/z=271 (M+1).

1. additionTo a 500-mL round-bottomed flask was added silica gel 60 (21 g, 350 mmol)
2. temperaturethe flask was heated with a heat gun under high vacuum for 30 min
3. temperatureto cool to room temperature
4. stirringThe reaction mixture was stirred
5. temperatureat reflux for 4 hours
6. temperatureto cool to room temperature
7. filtrationfiltered
8. concentrationThe organic solution was concentrated under reduced pressure
9. customThe residue was triturated with hexane

ORD record

ord-131df875750b42da92dc8b5297c6c99b

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569341B2