Ethyl 4-chlorobenzoylformate → 5-(4-chlorophenyl)-4-hydroxy-5-methyl-3-phenylmethoxy-2(5H)-furanone

Participants

Reaction Steps

A total of 3.4 mL (10.2 mmol) of 3.0 M methylmagnesium iodide was added to a solution of 2.34 g (10 mmol) of ethyl 4-chlorobenzoylformate in THF in an analogous manner as described for the synthesis of 3,4-dihydroxy-5-methyl-5-phenyl-2(5H)-furanone to give prior to hydrogenolysis 1.3 g (40% yield) of 5-(4-chlorophenyl)-4-hydroxy-5-methyl-3-phenylmethoxy-2(5H)-furanone as a yellow oil: 1H NMR (CDCl3) δ 7.37-7.21 (m, 9H), 5.10 (s, 2H), 1.73 (s, 3H).

Provenance & Evidence