4-Chlorobenzaldehyde → HCID 54040399, compound

To a suspension of 3-((2-methoxy)-2-propoxy)propyl)triphenyl phosphonium bromide (4.42 g, 10 mmoles) in THF (100 mL) was added n-BuLi (6 mL of 1.6M) at -78°. The reaction mixture was stirred at -78° for 30 min. 4-Chlorobenzaldehyde (1.4 g, 10 mM) was added and the reaction was warmed to RT. The reaction mixture was quenched with buffer and extracted with ethyl acetate. After evaporation of the ethyl acetate, the crude residue was dissolved in 25 mL THF and 5 mL of AcOH plus 5 mL H2O was added. The mixture was stirred for 2 hours at RT and evaporated. The residue was extracted with ethyl acetate, and the ethyl acetate evaporated. Flash chromatography of the residue using 25% ethyl acetate/hexane afforded the title compound as a mixture of cis and trans isomers.

1. customThe reaction mixture was quenched with buffer and
2. extractionextracted with ethyl acetate
3. customAfter evaporation of the ethyl acetate
4. dissolutionthe crude residue was dissolved in 25 mL THF
5. addition5 mL of AcOH plus 5 mL H2O was added
6. stirringThe mixture was stirred for 2 hours at RT
7. customevaporated
8. extractionThe residue was extracted with ethyl acetate
9. customthe ethyl acetate evaporated

ORD record

ord-4a6542f5319242d9937099d250830257

Source dataset

uspto-grants-1992_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05102881