Chloromethyl Methyl Ether → HCID 58598281, compound

Participants

Reaction Steps

Sodium hydride (60%, 513 mg, 12.84 mmol) was added to a solution of 4-{1-ethyl-1-[3-methyl-4-((E)-4,4,4-trifluoro-3-hydroxy-3-trifluoromethyl-1-butenyl)-phenyl]-propyl}-2-methyl-phenol (Example 26-(1); 5.91 g, 12.84 mmol) in N,N-dimethylformamide (60 mL) in a nitrogen atmosphere at room temperature, and the mixture was stirred for 30 minutes. Then, methoxymethyl chloride (1.45 mL, 19.26 mmol) was added, and the mixture was stirred at room temperature for 30 minutes and at 60° C. for 30 minutes. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, followed by extraction with ethyl acetate. The organic layer was washed with water and brine and then dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=20:1, 10:1 and 4:1) to give the target product as a colorless oil (2.14 g, 33%).

Provenance & Evidence