Imidazole → 9-Methoxymethyl-9-[(tert-butyldimethylsilyl)oxymethyl]-fluorene

Beteiligte Stoffe

Reaktionsschritte

1 g of 9-methoxymethyl-9-hydroxymethyl-fluorene (4.16 mmol) was dissolved in 10 ml of N,N-dimethyl formamide, and 0.14 g (2.08 mmol) of imidazole was added thereto. The solution was cooled in ice-water bath to below 5° C., and 0.87 ml of triethyl amine (6.24 mmol) was added thereto. After stirring for 5 minutes, 0.88 g of tert-butyldimethylsilyl chloride (5.82 mmol) in 10 ml of N,N-dimethyl formamide was added drop-wise to the reaction mixture, and the mixture was stirred for further 2 hours, followed by stirring at room temperature for 1 hour. The reaction mixture was diluted with 10 ml of water, and extracted using 30 ml of dichloromethane. The organic phase was wished twice with 20 ml of water, dried over anhydrous sodium sulfate. After filtration, the filtrate was evaporated to give 1.28 g of 9-methoxymethyl-9-[(tert-butyldimethylsilyl )oxymethyl]-fluorene crude product as pale yellow liquid. The crude product was purified by column chromatography using petroleum ether as eluent, to give colorless pure compound.

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