Reaktion #49353

Reaktionsgleichung

TMEDA

sec-butyllithium hexane

DMF

3-methoxy-N-(1-methyl-1-phenylethyl)benzamide

→

4-methoxy-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone

Ausbeute 66.0%

6-methoxy-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone

Ausbeute 17.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigefollowed by purification by flash column chromatography (hexane/ethyl acetate=2/1, 1/1)

Vorschrift

In a similar manner to Step 2 of Example 16, 3-methoxy-N-(1-methyl-1-phenylethyl)benzamide (6.00 g, 22.3 mmol) was dissolved in THF (240 mL), and the solution was treated with TMEDA (10.8 mL, 71.3 mmol), sec-butyllithium-hexane solution (0.99 mol/L, 72.0 mL, 71.3 mmol) and DMF (3.80 mL, 49.0 mmol), followed by purification by flash column chromatography (hexane/ethyl acetate=2/1, 1/1) to obtain 4-methoxy-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone (4.36 g, yield 66%) and 6-methoxy-3-hydroxy-2-(1-methyl-1-phenylethyl)isoindolinone (1.12 g, yield 17%).

Quelle