Sodium hydride → isopropyl-4-[(E)-1-(4-fluorobenzoyl)-4-phenyl-3-butenyl]benzoate

To a solution of isopropyl-4-[2-(4-fluorophenyl)-2-oxoethyl]benzoate(0.970 g, 3.23 mmol) in DMF (10 ml) at 0° C. was added NaH (0.100 g, 4.16 mmol). After a period of 0.5 h to the reaction mixture was added a solution of cinnamyl bromide (0.630 g, 3.21 mmol) in DMF (10 ml), and the reaction was stirred at room temperature for 1 hour. Saturated ammonium acetate solution (20 ml) was added and the mixture was extracted with ethyl acetate (20 ml). The organic phase was washed with brine and dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by flash chromatography using a gradient from hexane/ethyl acetate 2% to hexanel ethyl acetate 10% giving 0.39 g of the title compound.

1. extractionthe mixture was extracted with ethyl acetate (20 ml)
2. washThe organic phase was washed with brine
3. dry with materialdried over sodium sulfate
4. filtrationfiltered
5. customevaporated to dryness
6. customThe residue was purified by flash chromatography

ORD record

ord-b553de4fae04436881e623acce1a870f

Source dataset

uspto-grants-2003_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06583126B2