Water → 2-[[5-[[(2,2-Dimethyl-1,3-dioxolan-4-yl)-methoxy]methyl]tetrahydro-2-furanyl]-methoxy]-N,N-dipropylacetamide

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Reaction Steps

A mixture of 4.93 g of 5-[[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]methyl]tetrahydro-2-furan-methanol (0.02 mole) and 3.55 g of 2-chloro-N,N-dipropylacetamide (0.02 mole) are dissolved in 125 ml of dry dimethyl sulfoxide and the mixture stirred at room temperature under nitrogen. Slowly 0.50 g of sodium hydride (0.02 mole) is added to the dimethyl sulfoxide mixture and the reaction allowed to stir at ambient temperature (23°). After stirring for 10 minutes an exothermic reaction begins to take place and an ice-bath is used to maintain the reaction temperature below 30°. After stirring for 1 hour the ice-bath is removed and the reaction allowed to stir at room temperature for 18 hours. The excess NaH is destroyed by adding 5 ml of methanol and the entire reaction mixture is then poured into 400 ml of water. The product is extracted with 3×125 ml portions of chloroform. The CHCl3 extracts are combined and washed with 4× 300 ml portions of water. The CHCl3 layer is separated and dried over anhydrous Na2SO4 overnight. The CHCl3 is then removed in vacuo yielding a pale yellow oil which is vacuum distilled through a 10 cm vigreux column and the fraction distilling at 91°-94° @ 0.4 mm is collected, yielding 4.86 g (63%) of the above compound.

Provenance & Evidence