Diethyl Ether → HCID 11446346, compound

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.

1. temperaturethe mixture was refluxed for 2 hr
2. customthe ether phase was collected
3. washThe resultant ether solution was washed with a saturated saline solution
4. dry with materialdried over magnesium sulfate
5. customthe solvent was removed from the dried ether solution by distillation
6. customthe resultant residue was purified by a silica gel column chromatography through the use of hexane-ethyl acetate as a developing solvent
7. dissolutionThe purified product was dissolved in an ether, and 2N sodium hydroxide
8. additionwas added
9. temperatureThe mixture was refluxed for hydrolysis and decarboxylation
10. extractionthe reaction product was extracted with ethyl acetate
11. customThe solvent was removed from the extract
12. dissolutionthe resultant residue was dissolved in THF
13. additiona few drops of sulfuric acid was added
14. concentrationthe solution was concentrated
15. customthe solute was purified from the
16. concentrationconcentrate by a silica gel column chromatography through the use of a mixed solution

ORD record

ord-ddc90518eed24d3ea04a6196ceb8436c

Source dataset

uspto-grants-1996_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05480580