Dimethylformamide → 4-Methoxymethoxy-5-methyl-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone

Participants

Reaction Steps

In a similar manner to Step 2 of Example 16, 3-methoxymethoxy-4-methyl-N-(1-methyl-1-phenylethyl)benzamide (3.40 g, 10.9 mmol) was dissolved in THF (130 mL), and the solution was treated with TMEDA (5.20 mL, 34.5 mmol), sec-butyl lithium-hexane solution (0.95 mol/L, 36.5 mL, 34.7 mmol) and DMF (1.85 mL, 23.9 mmol), followed by purification by flash column chromatography (hexane/ethyl acetate=4/1 to 7/3 to 6/4). The obtained solid was purified by slurry using isopropylether and hexane to obtain 4-methoxymethoxy-5-methyl-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone (2.96 g, yield 80%).

Provenance & Evidence