Hydrogen Sulfide → 2-Carboxy-2-[(acetylthio)methyl]-1,2,3,4-tetrahydronaphthalene

HRID 1656055

Reaktionsgleichung

Reaktionsgleichung von HRID 1656055
[C:1]([C:4]1([CH2:14][S:15][C:16]([CH3:19])(C)C)[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)([OH:3])=[O:2].S.C(OC(=O)C)(=[O:23])C>FC(F)(F)C(O)=O.C(OCC)C>[C:1]([C:4]1([CH2:14][S:15][C:16](=[O:23])[CH3:19])[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)([OH:3])=[O:2]

Komponenten

6

Edukt 3

HCID 402Hydrogen SulfideHCID 7918Acetic AnhydrideHCID 197899372-Carboxy-2-(t-butyl)thiomethyl-1,2,3,4-tetrahydronaphthalene

Produkt 1

HCID 197899352-Carboxy-2-[(acetylthio)methyl]-1,2,3,4-tetrahydronaphthalene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

Dissolve 2-carboxy-2-(t-butyl)thiomethyl-1,2,3,4-tetrahydronaphthalene (5.36 g, 20.0 mmol) in trifluoroacetic acid (40 mL) and add mercuric acetate (6.36 g, 20.0 mmol). Stir at ambient temperature under an atmosphere of argon for 4.5 hours, then treat with gaseous hydrogen sulfide. Remove the resulting black solid by filtration and dilute the filtrate to 100 mL with methylene chloride. Wash with water, then with brine and dry (MgSO4). Evaporate the solvent in vacuo to a residue. Mix the residue with sulfuric acid (0.3 mL of 10% solution in acetic acid) and add acetic anhydride (2.04 g, 20.0 mmol). Stir the mixture for 2 hours under an atmosphere of argon at ambient temperature, then dilute with 100 mL ethyl ether. Wash with water, brine then dry (MgSO4). Concentrate the filtrate in vacuo to give the title compound.

Aufarbeitung

  1. customRemove the resulting black solid
  2. filtrationby filtration
  3. additiondilute the filtrate to 100 mL with methylene chloride
  4. washWash with water
  5. dry with materialwith brine and dry (MgSO4)
  6. customEvaporate the solvent in vacuo to a residue
  7. additionMix the residue with sulfuric acid (0.3 mL of 10% solution in acetic acid)
  8. stirringStir the mixture for 2 hours under an atmosphere of argon at ambient temperature
  9. washWash with water, brine
  10. dry with materialthen dry (MgSO4)
  11. concentrationConcentrate the filtrate in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6d978e2d64d849fdb074a8eecccb4ff5
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05252601

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