Water → HCID 66918669, Verbindung

HRID 1367479Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1367479
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[SH:10].[CH:11]1(OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:15][CH:14]=[CH:13][CH2:12]1.O>CN(C=O)C>[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][CH:14]1[CH2:13][CH:12]=[CH:11][CH2:15]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 80599o-ChlorothiophenolHCID 357673HCID 357673, Verbindung

Produkt 1

HCID 66918669HCID 66918669, VerbindungAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

NaH (316 mg, 55% in mineral oil, 7.24 mmol) was suspended in DMF (6 ml) and the suspension was cooled to 0° C. A solution of 2-chloro-thiophenol (880 ml, 97% purity, 7.55 mmol) in DMF (2 ml) was added dropwise. After stirring for 45 min at 0° C. a solution of toluene-4-sulfonic acid cyclopent-3-enyl ester (1500 mg, 6.29 mmol) in DMF (3 ml) was added dropwise and the reaction mixture was stirred at room temperature for 2 days. Water was added and the mixture was extracted 3 times with EtOAc. The combined organic layers were washed with water, saturated NaHCO3 solution and brine, dried over Na2OS4 and evaporated. The remaining brown oil was purified by silica gel chromatography (heptane/EtOAc 100:0-99:1) to obtain the title compound (1.047 g, 79%) as colorless liquid.

Aufarbeitung

  1. additionwas added dropwise
  2. extractionthe mixture was extracted 3 times with EtOAc
  3. washThe combined organic layers were washed with water, saturated NaHCO3 solution and brine
  4. dry with materialdried over Na2OS4
  5. customevaporated
  6. customThe remaining brown oil was purified by silica gel chromatography (heptane/EtOAc 100:0-99:1)

Quellen und Nachweise

ORD-Eintrag
ord-f2a008a51b2043f6a0f4796cddc43fce
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893099B2

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