Methoxymethyl-triphenylphosphonium chloride → 3-Methyl-4-(4-methylphenyl)-3-pyridin-3-ylbutanal

Under N2 Lithium bis(trimethylsilyl)amide solution (10.5 ml, 10.5 mmol, 1.0M in THF) was added to a mixture of methoxy methyltriphenyl phosphonium chloride (3.43 g, 10 mmol) in 25 ml THF dropwise at 0° C. After 15 min, it was added to a solution of the product of STEP 4 (1.65 g, 6.5 mmol) in 15 ml THF at 0° C. The reaction was stirred for 1 h and quenched with brine. The product was extracted with ethyl acetate. The organic layer was concentrated. The residue was dissolved in 50 ml THF and 50 ml 2N HCl solution. The reaction was stirred at room temperature for 18 h, and THF was evaporated. The residue was dilute with ethyl acetate and basified with 1N NaOH solution. The product was extracted thoroughly with ethyl acetate. The organic layer was washed with brine, and dried with MgSO4, and concentrated. The residue was purified by chromatography (on silica gel, ethyl acetate/hexane=3/1) to yield a brown oil in 1.37 g. NMR spectra of the product were consistent for the proposed structure.

1. customquenched with brine
2. extractionThe product was extracted with ethyl acetate
3. concentrationThe organic layer was concentrated
4. dissolutionThe residue was dissolved in 50 ml THF
5. stirringThe reaction was stirred at room temperature for 18 h
6. customTHF was evaporated
7. additionThe residue was dilute with ethyl acetate and basified with 1N NaOH solution
8. extractionThe product was extracted thoroughly with ethyl acetate
9. washThe organic layer was washed with brine
10. dry with materialdried with MgSO4
11. concentrationconcentrated
12. customThe residue was purified by chromatography (on silica gel, ethyl acetate/hexane=3/1)
13. customto yield a brown oil in 1.37 g

ORD record

ord-fabe6cca8e7249df8fca6f17ad2f2150

Source dataset

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06531494B1