Sodium hydride → HCID 21746905, compound

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Reaction Steps

In 50 ml of anhydrous tetrahydrofuran, is dissolved 1.32 g of trans-3-hydroxy-6-cyano-3,4-dihydro-2,2-dimethyl-4-(1,2-dihydro-2-oxo-5-t-butyldimethylsilyloxymethyl-1-pyridinyl)-2H-benzo[b]pyran obtained in Example 12. Then, 0.12 g of 60% oily sodium hydride is added to the solution at room temperature, and reacted under reflux for 3 hours. The reaction mixture is concentrated under reduced pressure, and the residue is mixed with ethyl acetate and water and extracted with the ethyl acetate. The organic layer is successively washed with water and saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The inorganic matter is filtered off, and the filtrate is concentrated under reduced pressure. The residue is purified by silica gel column chromatography using 1/3 mixture of ethyl acetate/methylene chloride as a developing solvent to obtain 1.16 g of 6-cyano-2,2-dimethyl-4-(1,2-dihydro-2-oxo-5-t-butyldimethylsilyloxymethyl-1-pyridinyl}-2H-benzo[b]pyran.

Provenance & Evidence