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Sodium Bicarbonate → Ethyl 2-(9-benzyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indol-2-yl)acetate

HRID 1417483
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1417483
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2[CH2:17][CH2:18][CH:19]([CH2:21][C:22]3[O:23][CH2:24][C:25](C)(C)N=3)[S:20][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[OH:30].[Na+]>S(=O)(=O)(O)O.C(O)C>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2[CH2:17][CH2:18][CH:19]([CH2:21][C:22]([O:23][CH2:24][CH3:25])=[O:30])[S:20][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 516892Sodium BicarbonateHCID 57015605HCID 57015605, Verbindung

Produkt 1

HCID 53821095Ethyl 2-(9-benzyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indol-2-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

60 mg of 2-(9-benzyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indol-2-yl)methyl-4,4-dimethyl-2-oxazoline (prepared as described in Example 81) was dissolved in 5% v/v sulfuric acid in ethanol, and the mixture was refluxed for 6 hours. After this time, the reaction mixture was neutralized by the addition of a saturated aqueous solution of sodium hydrogencarbonate and then extracted with ethyl acetate. The ethyl acetate fraction was then washed with water and dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure, and the resulting residue was purified by silica gel column chromatography, using a mixture of 20% v/v ethyl acetate in hexane as the eluent, to afford 46 mg of the title compound as an oil.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 6 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate fraction was then washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was then removed by evaporation under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography
  7. additiona mixture of 20% v/v ethyl acetate in hexane as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-189730aed94544008687704c460bcd28
Quelldatensatz
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05877199

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