Thiophenol → Ethyl 3-oxo-4-(phenylthio)cyclohexanecarboxylate

HRID 1593615Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1593615
Br[CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][C:3]1=[O:13].[C:14]1([SH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[Na+]>CCO>[O:13]=[C:3]1[CH:2]([S:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4]1

Komponenten

5

Edukt 3

HCID 7969ThiophenolHCID 14798Sodium HydroxideHCID 12917736Ethyl 4-bromo-3-oxocyclohexanecarboxylate

Produkt 1

HCID 58999613Ethyl 3-oxo-4-(phenylthio)cyclohexanecarboxylateAusbeute 61,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

To a solution of ethyl 4-bromo-3-oxocyclohexanecarboxylate (3.73 g, 15 mmol) in EtOH (30 mL) at 80° C. was added a solution of benzenethiol (1.65 mL, 15 mmol) and NaOH (0.6 g, 15 mmol) in EtOH (100 mL). The suspension was stirred for 1 hour, then was concentrated in vacuo. The residue was diluted with water and extracted with EtOAc. The organic layer was washed with water then brine, then was dried over MgSO4 and concentrated in vacuo. Purification by chromatography on silica gel afforded 2.56 g (61%) of the title compound as a yellow oil: MS (−) 277 (M−H)−.

Aufarbeitung

  1. concentrationwas concentrated in vacuo
  2. additionThe residue was diluted with water
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water
  5. dry with materialbrine, then was dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-5fe8248b5ef84d848efa74c3fdf50697
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07297704B2

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