Ammonium Chloride → HCID 86661753, compound

Participants

Reaction Steps

(2R)-(2-trifluoroacetamidopropyl)triphenylphosphonium iodide (8.3 g) synthesized according to J. Med. Chem. 2007, 50, 5627-5643 was dissolved in anhydrous tetrahydrofuran and cooled to −78° C. n-butyllithium (1.6 M n-hexane solution, 18.7 mL) was slowly added dropwise. After the dropwise addition, the mixture was stirred at room temperature for 20 minutes. Subsequently, the mixture was cooled to −78° C., and an anhydrous tetrahydrofuran (10 mL) solution of 2-benzyloxyacetaldehyde (2.35 g) was added. The mixture was gradually returned to room temperature and stirred at room temperature for 12 hours. After the completion of reaction, a saturated aqueous solution of ammonium chloride was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to obtain the compound of interest as a pale yellow oil (2.30 g, 52.6%).

Provenance & Evidence