Acetyl chloride → HCID 77141723, compound

Acetyl chloride (19.4 mL, 274.4 mmol) was slowly added at 0° C. to methanol (120.0 mL) under stirring. A solution of 4-(2-chloro-phenyl)-2-oxo-3-butenoic acid (17.0 g, 80.7 mmol) prepared in Step 1 in methanol (80.0 mL) was added to the reaction mixture at room temperature. The reaction mixture was stirred at room temperature for 1 hour, additionally at 80° C. for 16 hours. The reaction mixture was concentrated under reduced pressure and then ethyl acetate was added thereto. The reaction mixture was washed with distilled water and brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/8) to give 7.2 g of the titled compound as a yellow solid.

1. stirringThe reaction mixture was stirred at room temperature for 1 hour, additionally at 80° C. for 16 hours
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. additionethyl acetate was added
4. washThe reaction mixture was washed with distilled water and brine
5. dry with materialdried on anhydrous magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customto give a yellow liquid residue
8. customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/8)

ORD record

ord-964046b3b79f44bdb512b991ba0b9734

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09376420B2