18-Crown-6 → HCID 13415102, compound

Temperature

-78 °C

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.

1. additionwas added
2. stirringthe mixture was stirred at room temperature for 1 hr
3. extractionextracted with ethyl acetate
4. washThe extract was washed with saturated brine
5. customdried
6. concentrationconcentrated under reduced pressure
7. customThe residue was separated
8. custompurified by silica gel column chromatography (solvent gradient; 5→15% ethyl acetate/hexane)

ORD record

ord-d414df6e49e94ad7aef2aad45ab2a436

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592454B2