Oxalyl chloride → HCID 23288301, compound

Temperature

-78 °C

A solution of 4-(3,4-dichlorophenyl)-4-oxo-2-butencarboxylic acid (2.0 g, 8.16 mmol) and oxalyl chloride (0.84 ml, 9.79 mmol) in chloroform (25 ml), was maintained at room temperature under nitrogen atmosphere for 3 hours. The solvent was removed under vacuum and the residue evaporated twice from toluene with the rotary evaporator to remove traces of oxalyl chloride. The thus obtained acid chloride was dissolved in methylene chloride (15 ml) and cooled at -78° C., under inert atmosphere. TEA (1.25 ml, 9.79 mmol), 4-DMAP (0.1 g, 0.816 mmol) and 4-methoxy benzylamine (1.12 g, 8.16 mmol) were added while magnetic stirring was continued at -78° C. for 4 hours. The reaction mixture was allowed to warm at room temperature and then diluted with methylene chloride (100 ml); the organic phase was washed with 1N HCl (3×10 ml), saturated potassium bicarbonate (3×10 ml), brine (3×15 ml), dried over anhydrous sodium sulphate and concentrated under vacuum. The residue was purified by flash chromatography, using cyclohexane/ethyl acetate 0÷5 as eluent. The title compound was obtained as a light yellow solid (1.84 g, 62w) (m.p. 169°-170° C.).

1. customThe solvent was removed under vacuum
2. customthe residue evaporated twice from toluene with the rotary evaporator
3. customto remove traces of oxalyl chloride
4. dissolutionThe thus obtained acid chloride was dissolved in methylene chloride (15 ml)
5. temperatureto warm at room temperature
6. washthe organic phase was washed with 1N HCl (3×10 ml), saturated potassium bicarbonate (3×10 ml), brine (3×15 ml)
7. dry with materialdried over anhydrous sodium sulphate
8. concentrationconcentrated under vacuum
9. customThe residue was purified by flash chromatography

ORD record

ord-5b82f6ddd31547b3bc803a0fb9f1f6d5

Source dataset

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06133302