Diethyl Ether → HCID 11446346, compound

Participants

Reaction Steps

To a solution of 0.55 g of sodium in 20 ml of absolute ethanol were added 6 g of (S)-2,2-diethyl-4-(2-iodoethyl)-1,3-dioxolane synthesized in Example 1 and 3.7 g of diethyl malonate, and the mixture was refluxed for 2 hr. Then, 50 ml of an ether and 50 ml of water were successively added to the resultant solution, and the ether phase was collected. The resultant ether solution was washed with a saturated saline solution, dried over magnesium sulfate, the solvent was removed from the dried ether solution by distillation, and the resultant residue was purified by a silica gel column chromatography through the use of hexane-ethyl acetate as a developing solvent. The purified product was dissolved in an ether, and 2N sodium hydroxide was added thereto. The mixture was refluxed for hydrolysis and decarboxylation, the pH was adjusted to 5 with 1N hydrochloric acid, and the reaction product was extracted with ethyl acetate. The solvent was removed from the extract, the resultant residue was dissolved in THF, a few drops of sulfuric acid was added thereto, the solution was concentrated, and the solute was purified from the concentrate by a silica gel column chromatography through the use of a mixed solution comprising hexane and ethyl acetate as a developing solution to obtain 0.7 g of (S)-5-hydroxymethyl-valerolactone.

Provenance & Evidence