Hydrochloric Acid → Dimethyl[(2-methyl-1,3-dithiolan-2-yl)methyl]propanedioate

HRID 235691

Reaktionsgleichung

Reaktionsgleichung von HRID 235691
[CH3:1][C:2]1([CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])[S:6][CH2:5][CH2:4][S:3]1.[C:13](=O)([O:16]C)[O:14][CH3:15].[H-].[Na+].Cl.[Cl-].[Na+]>O1CCCC1>[CH3:12][O:11][C:9](=[O:10])[CH:8]([CH2:7][C:2]1([CH3:1])[S:3][CH2:4][CH2:5][S:6]1)[C:13]([O:14][CH3:15])=[O:16]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 10921676Methyl 2-methyl-1,3-dithiolane-2-propanoate

Produkt 1

HCID 20219600Dimethyl[(2-methyl-1,3-dithiolan-2-yl)methyl]propanedioateAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of about 160 g of methyl 2-methyl-1,3-dithiolane-2-propanoate, about 174.63 g of dimethyl carbonate, about 74.41 g of sodium hydride and about 1000 ml of tetrahydrofuran was refluxed for about 19 hours under argon. The mixture was cooled to room temperature, added to a mixture of ice and dilute hydrochloric acid (about 1N) with stirring and saturated with sodium chloride. The organic layer was washed with saturated sodium bicarbonate then saturated sodium chloride, dried and the solvent removed. The residue was dissolved in ether, treated with charcoal, filtered through silica gel and the solvent removed. The residue was distilled via a Kugelrohr collecting the major fraction at about 180°-190° C., at about 0.5 mm giving about 96.26 g of the desired title product as a yellow oil.

Aufarbeitung

  1. temperaturewas refluxed for about 19 hours under argon
  2. washThe organic layer was washed with saturated sodium bicarbonate
  3. dry with materialsaturated sodium chloride, dried
  4. customthe solvent removed
  5. dissolutionThe residue was dissolved in ether
  6. additiontreated with charcoal
  7. filtrationfiltered through silica gel
  8. customthe solvent removed
  9. distillationThe residue was distilled via a Kugelrohr
  10. customcollecting the major fraction at about 180°-190° C.

Quellen und Nachweise

ORD-Eintrag
ord-8ebaee04aedf42ffb0c31d2e025e4f2c
Quelldatensatz
uspto-grants-1987_02
Patentnummer
US04640913

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