Acetic Acid → alpha-Mercaptomethyl-beta-phenyl-gamma-butyrolactone

HRID 65263

Reaktionsgleichung

Reaktionsgleichung von HRID 65263
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][O:12][C:10](=[O:11])[CH:9]2[CH2:14]OS(C)(=O)=O)=[CH:4][CH:3]=1.C(O)(=O)C.[SH-:24].[Na+]>C(O)C.C(OCC)(=O)C>[SH:24][CH2:14][CH:9]1[CH:8]([C:5]2[CH:4]=[CH:3][CH:2]=[CH:7][CH:6]=2)[CH2:13][O:12][C:10]1=[O:11]

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 28015Sodium hydrosulfideHCID 13518915beta-(p-Chlorophenyl)-alpha-methanesulfonyloxymethyl-gamma-butyrolactone

Produkt 1

HCID 13518975alpha-Mercaptomethyl-beta-phenyl-gamma-butyrolactoneAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 1.0 g of α-methanesulfonyloxymethyl-β-phenyl-γ-butyrolactone (III) in 20 ml of ethanol were added 1.5 ml of acetic acid and then 1.2 g of commercially available 70% sodium hydrosulfide and the mixture was stirred at room temperature for 18 hours. After completion of the reaction, the reaction mixture was diluted with 150 ml of ethyl acetate, washed with water in a conventional manner, dried over magnesium sulfate and the solvent was distilled off. The crude product thus obtained was purified by a column chromatography to give 400 mg (yield 52%) of the title compound.

Aufarbeitung

  1. customAfter completion of the reaction
  2. washwashed with water in a conventional manner
  3. dry with materialdried over magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe crude product thus obtained
  6. customwas purified by a column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-62844afc2adb4bd9bea5546d1bc4665b
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04613613

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