Water → 2-(2,2-Diethoxyethyl)-1,3-propanediol

Participants

Reaction Steps

To a cooled suspension (0° C.) of lithium aluminum hydride (4.9 g, 0.129 mol) in anhydrous tetrahydrofuran (80 mL), was added a solution of diethyl 2,2-diethoxyethylmalonate (17.6 g, 63.7 mmol) in anhydrous tetrahydrofuran (60 mL), and the mixture was stirred 3 h at room temperature. Then, the reaction mixture was immersed in an ice bath and a mixture of water (4.6 mL) and tetrahydrofuran (9.2 mL) was added dropwise followed by a solution of 15% sodium hydroxide (4.6 mL) and water (12.5 mL). After stirring for 20 minutes, the suspension was filtered off, the solvent was removed at reduced pressure, and 300 mL of chloroform was added. The solution was dried over sodium sulfate and after removal of the solvent, 8.8 g of a white solid was obtained and used in the next step without further purification.

Provenance & Evidence