Toluene → HCID 19360032, compound

Participants

Reaction Steps

5-Hydroxy-4-[2-(3-methoxyphenoxy)phenyl]-2-methyl-3(2H)-isoxazolone (2.5 g) was dissolved in 3 mL of methanol and 15 mL of toluene and cooled in an icebath. Trimethylsilyldiazomethane (5 mL of a 2.0M solution in hexane) was added dropwise. Gas evolution was observed. The resulting yellow solution was stirred at room temperature overnight. The solvents were removed under reduced pressure and the residue was purified by flash chromatography (1:1 hexane:ethyl acetate as eluant). The second eluting component was collected to yield 950 mg (36%) of the title compound of Step D. 1H NMR (CDCl3): δ7.51 (dd,J=1.7, 7.5Hz,1H), 7.27 (dt,J=1.7, 7.5Hz,1H), 7.17 (m,2H), 6.97 (dd,J=1, 8Hz,1H), 6.5 (m,3H), 3.92 (s,3H), 3.74 (s,3H), 3.33(s,3H).

Provenance & Evidence