Ammonium Chloride → (S)-3-((R,Z)-6-(Benzyloxy)-2-(4-fluoro-3-methylphenoxy)hex-4-enoyl)-4-isopropyloxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

To the solution of lithium bis(trimethylsilyl)amide (1.2 mL, 1.2 mmol, 1M in THF) in anhydrous 20 mL THF at −70° C. was slowly added over 15 minutes (S)-3-(2-(4-fluoro-3-methylphenoxy)acetyl)-4-isopropyloxazolidin-2-one (295 mg, 1.0 mmol) as a solution in 3.0 mL THF. The reaction mixture was stirred for 30 min at −70° C. and then was slowly added a pre-cooled solution of (4-Iodo-but-2-enyloxymethyl)-benzene (576 mg, 2.0 mmol) in 3 mL of THF. The resulting mixture was stirred at −70° C. for 1 h and the temperature was slowly raised over a period of 2 h. The mixture was poured into 20 mL saturated NH4Cl and extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with brine (2×20 mL) and dried over Na2SO4. The solvent was removed under reduced pressure and the product isolated by Flash column chromatography eluting with 0% to 50% ethyl acetate/hexane to give 294 mg of the title compound as a light yellow oil.

Provenance & Evidence