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

HRID 1593615Notes

Reaction equation

HRID 1593615 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 58999613Ethyl 3-oxo-4-(phenylthio)cyclohexanecarboxylateYield 61.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

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)−.

Workup

  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

Sources & evidence

ORD record
ord-5fe8248b5ef84d848efa74c3fdf50697
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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