((7-Chloroquinolin-2-yl)methyl)triphenylphosphonium bromide → Methyl 3-((1-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(2-hydroxy-2-propyl)phenyl)propyl)thio)-2-methylpropanoate

Participants

Reaction Conditions

Reaction Steps

To ((7-chloro-2-quinolinyl)methyl)triphenylphosphonium bromide (525 mg, 1.01 mmol, U.S. Pat. No. 4,851,409, Example 4, Step 2) in a THF (2 mL) solution at -78° C. was added dropwise 1.6M nBuLi (472 mL, 0.945 mmol). After a few minutes, the aldehyde of Step 11 (140 mg, 0.338 mmol) was then added and the resulting mixture was stirred at -78° C. for 30 min. The reaction mixture was then allowed to warm to r.t. for 30 min and was quenched by the addition of 25% aq NH4OAc. The title product was then extracted with EtOAc, dried on Na2SO4 and evaporated under reduced pressure. After purification by flash chromatography (20% EtOAc in toluene), the title compound was obtained as an oil (170 mg, 89%).

Provenance & Evidence