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

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.

1. temperatureto warm to room temperature
2. customquenched with 5%Na2SO3 solution (200 ml)
3. extractionThe product was extracted with ethyl acetate (3×100 ml)
4. washThe organic layer was washed with H2O, brine
5. dry with materialdried with MgSO4
6. concentrationconcentrated
7. customThe residue was purified by chromatography (on silica gel, ethyl acetate/hexane=1/1)
8. customto give a brown liquid in 11.7 g

ORD-Eintrag

ord-c3830d08ce7d4b9ea83abf508fda102f

Quelldatensatz

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06531494B1