Phenylacetone → Ethyl 4-(1-hydroxy-1-methyl-2-phenylethyl)-3-nitrobenzoate

Participants

Reaction Steps

According to Example 2, the Grignard reagent 1e (freshly prepared via iodine-magnesium exchange[6] from ethyl-4-iodo-3-nitrobenzoate (353 mg, 1.10 mmol; 1.10 equiv) and PhMgCl.LiCl (0.95 M in THF; 1.13 mL, 1.07 mmol, 1.07 equiv) at −50° C.) was reacted with 1-phenyl-propan-2-one (201 mg; 1.00 mmol) in the presence of LaCl3.2LiCl (0.33 M; 3.03 mL, 1.00 mmol, 1.00 equiv). The crude product was purified by flash column chromatography (silica; pentane:Et2O, 19:1) to give the desired product as yellow oil (231 mg, 73%).

Provenance & Evidence