Ammonium Chloride → HCID 68433868, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of triphenyl(tetrahydro-2H-pyran-4-ylmethyl)phosphonium iodide (5.11 g) in dry tetrahydrofuran (20 mL) was added lithium hexamethyldisilazide (1.1M tetrahydrofuran solution, 9.1 mL), and the mixture was stirred at 15° C. for 2 hr. To the reaction mixture was added a solution of ethyl [5-(methylsulfanyl)pyridin-2-yl](oxo)acetate (2.05 g) in dry tetrahydrofuran (20 mL), and the mixture was stirred at room temperature for 16 hr. A saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and the title compound (2.41 g, yield 86%) was obtained as yellow amorphous crystals from a fraction eluted with ethyl acetate-hexane (1:2, volume ratio).

Provenance & Evidence