Sodium hydride → 2-(((Tert-butyldimethylsilyl)oxy)methyl)prop-2-en-1-ol

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Reaction Steps

Under argon atmosphere, to a suspension of sodium hydride (490 mg, 60 wt. % oil dispersion) in tetrahydrofuran (10 ml) were sequentially added 2-methylene-1,3-propanediol (1 ml) and tert-butyldimethylchlorosilane (2.22 g) at 0° C., and then the mixture was stirred at room temperature for 1 hour. To this reaction mixture was added a saturated aqueous solution of ammonium chloride, and the mixture was extracted with ethyl acetate. This organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/1) to give the titled compound (1.62 g).

Provenance & Evidence