Potassium Carbonate → HCID 178458880, compound

HRID 703361Notes

Reaction equation

HRID 703361 reaction equation
[OH:1][C:2]1[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][C:11]([SH:14])=[CH:10][CH:9]=2)[CH2:5][C:4](=[O:15])[C:3]=1[C:16](=[O:19])[CH2:17][CH3:18].CS([C:24]1[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][N:25]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O.[OH-].[Na+]>[C:16]([C:3]1[C:2](=[O:1])[CH2:7][CH:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14][C:24]3[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][N:25]=3)=[CH:10][CH:9]=2)[CH2:5][C:4]=1[OH:15])(=[O:19])[CH2:17][CH3:18]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 131026752,5-Bis(methylsulfonyl)pyridineHCID 178458882HCID 178458882, compound

Product 1

HCID 178458880HCID 178458880, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 8.0 g (0.029 mol) of 3-hydroxy-5-(4-mercaptophenyl)-2-propionyl-cyclohex-2-en-1-one in 150 mL of acetonitrile was added 6.80 g (0.0290 mol) of 2,5-bis(methylsulfonyl)pyridine and 8.0 g (0.0579 mol) of powdered potassium carbonate. The mixture was heated at reflux for 3 hours and cooled. The mixture was diluted with 500 mL of water and 50 mL of 1.0N NaOH and filtered through Celite®. The filtrate was acidified (pH 2) with concentrated HCl and extracted 4 times with 300 mL of methylene chloride. The organic layer was washed twice with 150 mL portions of water and dried over MgSO4. The solvent was removed in vacuo leaving 10.4 g (83 percent of theoretical) of the crude product which was purified by column chromatography using methylene chloride as the eluent. Recrystallization of the crude from ethanol gave the above named product in a yield of 5.10 g (41 percent of theoretical). The product melted at 167°-174° C.; 1H NMR (CF3CO2H): δ 1.25 (t, 3H, CH3CH2 --), 2.8-3.7 (m, 10H, ring protons and CH3SO2 --, CH3CH2 --), 7.3-8.9 (m, 7H, ArH).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hours
  3. temperaturecooled
  4. filtrationfiltered through Celite®
  5. extractionextracted 4 times with 300 mL of methylene chloride
  6. washThe organic layer was washed twice with 150 mL portions of water
  7. dry with materialdried over MgSO4
  8. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-459221458e2240abafdb6297bd9b1c26
Source dataset
uspto-grants-1991_01
Patent number
US04983211

Reaction notes

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