Water → 4-(9H-fluoren-9-ylmethyl)-2-methyl-2,3-dihydro-1H-inden-1-yl methyl ether

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Reaction Conditions

Reaction Steps

To a solution of 3.32 g (0.20 mol) of 9H-fluorene in 500 ml of ether 80 ml of 2.5 M (0.20 mol) n-BuLi in hexanes was added at 0° C. This mixture was stirred for 12 h, cooled to −80° C., and then a solution of 5.10 g (0.20 mol) of 4-(bromomethyl)-1-methoxy-2-methylindane in 150 ml of ether was added dropwise by vigorous stirring for 30 min at this temperature. The resulting mixture was stirred for 24 h at room temperature, and then 500 ml of water was added. The organic layer was separated, and the aqueous layer was extracted with 3×200 ml of dichloromethane. The combined organic extract was dried over Na2SO4 and evaporated to dryness. The product was isolated by flash chromatography on Silica Gel 60 (40-63 um, d 60 mm, l 150 mm; eluent: hexanes/ether=20/1). Yield 5.31 g (78%) of a mixture of the diastereomers A and B.

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