Phenol → HCID 24964144, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 3-(4-bromomethyl-benzyl)-5-(R)-phenyl-oxazolidin-2-one (30 mg, 0.086 mmol, prepared according to procedure 4), phenol (10 mg, 0.1 mmol), potassium carbonate (25 mg, 0.18 mmol), potassium iodide (3 mg, 0.008 mmol) and 2-butanone was heated at 80° C. overnight. The reaction mixture was allowed to cool down to RT, mixed with water (5 mL), organic phase was separated and the aq. phase was extracted with ethyl acetate (3×8 mL). The combined organic phase was washed with brine (5 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to get the product. Purification by chromatography on silica gel, eluting with 5-20% ethyl acetate in hexanes yielded the title compound (22 mg, 59%) as a white solid. 1H NMR (300 MHz, CDCl3): δ 7.38 (m, 11H), 6.99 (m, 3H), 5.50 (t, 1H), 5.08 (s, 2H), 4.59 (d, 1H), 4.44 (d, 1H), 3.80 (m, 1H), 3.34 (m, 1H).

Provenance & Evidence