Potassium Hydroxide → Ethyl 4-[(4-fluorophenyl)thio]-3-oxocyclohexanecarboxylate

HRID 1593614Notes

Reaction equation

HRID 1593614 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].[F:14][C:15]1[CH:20]=[CH:19][C:18]([SH:21])=[CH:17][CH:16]=1.[OH-].[K+]>CCO>[F:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][CH:2]2[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][C:3]2=[O:13])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 677894-FluorothiophenolHCID 12917736Ethyl 4-bromo-3-oxocyclohexanecarboxylate

Product 1

HCID 69232235Ethyl 4-[(4-fluorophenyl)thio]-3-oxocyclohexanecarboxylateYield 51%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of ethyl 4-bromo-3-oxocyclohexanecarboxylate (5.2 g, 20.9 mmol) in EtOH (120 mL) at 80° C. was added a solution of 4-fluorobenzenethiol (2.22 mL, 20.9 mmol) and KOH (1.29 g, 22.9 mmol) in EtOH (50 mL). The suspension was stirred for 30 min then filtered. The filtrate was concentrated in vacuo then diluted with water and extracted with diethyl ether. The organic layer was washed with water then brine, then was dried over MgSO4 and concentrated in vacuo. Purification by chromatography on silica gel (15% EtOAc in hexane) afforded the title compound (3.08 g, 51%) as a white solid: mp 96-97° C.; MS (+) 297 (M+H)+.

Workup

  1. filtrationthen filtered
  2. concentrationThe filtrate was concentrated in vacuo
  3. additionthen diluted with water
  4. extractionextracted with diethyl ether
  5. washThe organic layer was washed with water
  6. dry with materialbrine, then was dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customPurification by chromatography on silica gel (15% EtOAc in hexane)

Sources & evidence

ORD record
ord-cb0ca5ebfb5a44d4acdc83b3ed4b97d6
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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