Ethyl Propionate → HCID 18929409, compound

Temperature

0 °C

To 3.8 ml of anhydrous diisopropylamine in 50 ml anhydrous tetrahydrofuran was added 14.7 ml of n-butyllithium (1.61 moles/liter in hexane) at 0° C., the mixture was stirred at 0° C. for 30 minutes, and 2.4 ml of ethyl propionate in 10 ml of anhydrous tetrahydrofuran was thereafter added to the mixture. The resulting mixture was stirred at -78° C. for 1 hour, and 5.0 g of 2,6-dichloro-4-trifluoromethylbenzaldehyde (7) in 10 ml of anhydrous tetrahydrofuran was thereafter added to the mixture, followed by stirring at -78° C. for 30 minutes and then at room temperature for 1 hour. The reaction mixture was poured into ice water, followed by extraction with ethyl acetate, washing with brine, drying over anhydrous magnesium sulfate and concentration under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/6), affording 7.2 g of the desired product in the form of a yellow oil (yield 91.1%).

1. stirringThe resulting mixture was stirred at -78° C. for 1 hour
2. stirringby stirring at -78° C. for 30 minutes
3. waitat room temperature for 1 hour
4. extractionfollowed by extraction with ethyl acetate
5. washwashing with brine
6. dry with materialdrying over anhydrous magnesium sulfate and concentration under reduced pressure
7. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/6)

ORD record

ord-41a17ad884be4f0d9d9d0f72b2e7769e

Source dataset

uspto-grants-1998_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05739083