18-Crown-6 → HCID 13415102, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl [bis(2,2,2-trifluoroethoxy)phosphoryl]acetate (5.0 g) and 18-crown-6 (10.3 g) in THF (200 mL) was added dropwise at −78° C. potassium bis(trimethylsilyl)amide (15% toluene solution, 21 mL), and 4-fluorobenzaldehyde (1.95 g) was added. The reaction mixture was stirred at −78° C. for 20 min, and the mixture was stirred at room temperature for 1 hr. The mixture was diluted with saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The extract was washed with saturated brine, dried and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (solvent gradient; 5→15% ethyl acetate/hexane) to give methyl (2Z)-3-(4-fluorophenyl)prop-2-enoate (2.24 g, 79%) as a colorless oil.

Provenance & Evidence