Potassium Carbonate → Ethyl 4-[(4-bromophenyl)thio]-3-oxocyclohexanecarboxylate

HRID 1593642Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1593642
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH:16]1[CH2:21][CH2:20][CH:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:18][C:17]1=[O:27]>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH:16]2[CH2:21][CH2:20][CH:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:18][C:17]2=[O:27])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 660494-BromothiophenolHCID 12917736Ethyl 4-bromo-3-oxocyclohexanecarboxylate

Produkt 1

HCID 69249727Ethyl 4-[(4-bromophenyl)thio]-3-oxocyclohexanecarboxylateAusbeute 63,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

To a solution of 4-bromobenzenethiol (2.92 g, 15.45 mmol) in 20 mL acetone was added K2CO3 (2.2 g, 15.18 mmol) and a solution of ethyl 4-bromo-3-oxocyclohexanecarboxylate (3.73 g, 15 mmol) in acetone (10 mL). The resulting suspension was stirred at room temperature for 2 hour, and then was partitioned between water and hexane. The organic layer was washed with water, then brine, then was dried over MgSO4, filtered, and concentrated. Purification by chromatography on silica gel (15% EtOAc in hexane) afforded 3.4 g (61%) of the title compound as an oil: MS (ES) m/z=356 [M]+.

Aufarbeitung

  1. customwas partitioned between water and hexane
  2. washThe organic layer was washed with water
  3. dry with materialbrine, then was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by chromatography on silica gel (15% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-777c705b79ad4b9abdb9db43c20725ea
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07297704B2

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