Ethoxalyl chloride → HCID 59627701, compound

Temperature

0 °C

Ethyl 2-chloro-2-oxoacetate (6.43 mL, 57.47 mmol) was added dropwise to a stirred suspension of aluminum trichloride (7.66 g, 57.47 mmol) in DCM (60 mL) at 0° C., over a period of 5 minutes under nitrogen. The resulting suspension was stirred at 0° C. for 15 minutes. A solution of 1-chloro-2-methoxy-4-methylbenzene (5 g, 31.93 mmol) in DCM (50 mL) was added dropwise over a period of 5 minutes and the resulting mixture was stirred at 0° C. for 90 minutes. The reaction mixture was cautiously quenched with water (300 mL) at 0° C., extracted with EtOAc (2×200 mL), the organic layers were combined, dried over MgSO4, filtered and evaporated to afford cream solid. The crude solid was triturated with DCM to give a solid which was collected by filtration and dried under vacuum to give ethyl 2-(5-chloro-4-methoxy-2-methylphenyl)-2-oxoacetate (4.27 g) as a white solid. The residue was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford ethyl 2-(5-chloro-4-methoxy-2-methylphenyl)-2-oxoacetate (1.85 g,) as a white solid. Total yield of ethyl 2-(5-chloro-4-methoxy-2-methylphenyl)-2-oxoacetate (6.12 g, 74.7%).

1. stirringthe resulting mixture was stirred at 0° C. for 90 minutes
2. customThe reaction mixture was cautiously quenched with water (300 mL) at 0° C.
3. extractionextracted with EtOAc (2×200 mL)
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. customevaporated
7. customto afford cream solid
8. customThe crude solid was triturated with DCM
9. customto give a solid which
10. filtrationwas collected by filtration
11. customdried under vacuum

ORD record

ord-c8dc2bddd7a64d3e9dfa31b14fb4555b

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188092B2