Water → (4R,5R)-1,3-Dioxolane-4,5-dimethanol

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Reaction Steps

300 ml of diethyl ether was added to 25.75 g of lithium aluminum hydride, and the mixture was heated while refluxing. A solution of 130.46 g of (4S,5S)-4,5-bis (ethoxycarbonyl)-1,3-dioxolane (obtained in Example 2) in 100 ml of ether was slowly added dropwise to this mixture. After the addition, the refluxing was continued for further about one hour. After allowing the reaction mixture to cool, 30 ml of water was slowly added under ice-cooling to decompose an excessive amount of lithium aluminum hydride. Then, 30 ml of 4N aqueous solution of sodium hydroxide and 90 ml of water were added dropwise. The reaction mixture was filtered with suction and the precipitate was extracted with 1000 ml of an ethanol-dioxane mixture at about 60° C., followed by filtration of the extract with suction. This procedure was repeated three times. The filtrate was concentrated to obtain crude (4R,5R)-4,5-bis(hydroxymethyl)-1,3-dioxolane.

Provenance & Evidence