4-Methyloxybenzyl chloride → Ethyl 2-methyl-3-(4-methylphenyl)-2-pyridin-3-ylpropanoate

Participants

Reaction Conditions

Reaction Steps

A solution of the product of STEP 1 (7.5 g, 42.1 mmol) was dissolved in 50 ml THF and a solution of lithium bis(trimethylsilyl)amide (45 ml, 45 mmol, 1.0 M in THF) was added dropwise at −70° C. The reaction was stirred at −70° C. for 1 h and a solution of 4-methoxybenzyl chloride (7.8 g, 50 mmol) in 25 ml THF was added. The reaction was allowed to warm to room temperature and quenched with 5%Na2SO3 solution (200 ml). The product was extracted with ethyl acetate (3×100 ml). The organic layer was washed with H2O, brine, dried with MgSO4, and concentrated. The residue was purified by chromatography (on silica gel, ethyl acetate/hexane=1/1) to give a brown liquid in 11.7 g. NMR spectra of the product were consistent for the proposed structure.

Provenance & Evidence