Hydrochloric Acid → HCID 11010838, compound

Temperature

-20 °C

Under an argon atmosphere, stirring and cooling at −20° C., titanium chloride (IV) (35.0 mL, 318 mmol) and dichloromethyl methyl ether (13.4 mL, 148 mmol) were added dropwise in sequence to a solution of ethyl 2-ethyl-3-(4-methoxyphenyl)propanoate (10.0 g, 42.3 mmol) in dichloromethane (500 mL). The mixture was stirred for 6 hours at −20° C. to −5° C. The reaction mixture was poured into a mixture of ice (600 g) with 3 mol/L hydrochloric acid (400 mL) and the dichloromethane layer was separated, which was washed with water and brine, dried over anhydrous sodium sulfate, and then concentrated. The residue was purified by silica gel column chromatography (eluent n-hexane:ethyl acetate=4:1 v/v) to afford 10.9 g (97%) of the title compound as a light brown oily product.

1. stirringThe mixture was stirred for 6 hours at −20° C. to −5° C
2. customthe dichloromethane layer was separated
3. washwhich was washed with water and brine
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated
6. customThe residue was purified by silica gel column chromatography (eluent n-hexane:ethyl acetate=4:1 v/v)

ORD record

ord-32f2a981c0a648bb96a0936d4661b3e2

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07049342B2