Reaction #47805

Reaction equation

6-Methoxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl ester

benzylmagnesium chloride

→

titled compound

Yield 13.0%

1-benzyl-1-hydroxy-6-methoxy-3-phenyl-1H-indene-2-carboxylic Acid Ethyl Ester

Yield 13.0%

Solvents

THF

Conditions

Workup

1. 1
   WashThe resulting mixture washed with saturated saline
2. 2
   Extractionextracted with ethyl acetate
3. 3
   OtherThe organic layer was separated
4. 4
   Dryingdried over anhydrous MgSO4
5. 5
   Concentrationconcentrated under a reduced pressure
6. 6
   OtherThe resulting residue was purified by flash chromatography

Procedure

6-Methoxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl ester (300 mg, 0.974 mmol) obtained in Example 1 was dissolved in THF and 1.2 equivalents of benzylmagnesium chloride were added thereto, followed by stirring for 3 hrs at 0° C. The resulting mixture washed with saturated saline and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous MgSO4, and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 50 mg of the titled compound (yield: 13%).

Source