4'-Hydroxyacetophenone → 1-(4-((5-(Cyclohexylsulfonyl)-2-pyridinyl)oxy)phenyl)ethanone

HRID 2290403Notes

Reaction equation

HRID 2290403 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=1.C1COCC1.CC([O-])(C)C.[K+].C1(S([C:31]2[CH:36]=[CH:35][C:34]([S:37]([CH:40]3[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41]3)(=[O:39])=[O:38])=[CH:33][N:32]=2)(=O)=O)CCCCC1>O>[CH:40]1([S:37]([C:34]2[CH:35]=[CH:36][C:31]([O:1][C:2]3[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][CH:3]=3)=[N:32][CH:33]=2)(=[O:39])=[O:38])[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45]1

Participants

6

Reactant 4

HCID 74694'-HydroxyacetophenoneHCID 8028TetrahydrofuranHCID 131026822,5-Bis(cyclohexylsulfonyl)pyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 131027121-(4-((5-(Cyclohexylsulfonyl)-2-pyridinyl)oxy)phenyl)ethanoneYield 31%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 3.68 g of p-hydroxyacetophenone in a 25 ml THF/25 ml DMSO mixture was added 3.2 g of t-BuOK and then 10.03 g of 2,5-bis(cyclohexylsulfonyl)pyridine, and the resulting mixture was heated at 62° C. for 11/2 hrs. The reaction mixture was cooled overnight, then added to 4 volumes of water and the crude product which formed recovered by filtration. Recrystallization of the crude product from CH2Cl2 /ethanol gave the product, 1-(4-((5-(cyclohexylsulfonyl)-2-pyridinyl)oxy)phenyl)ethanone, (31% yield), as light yellow prisms, m.p. 116°-118° C.

Workup

  1. temperatureThe reaction mixture was cooled overnight
  2. customthe crude product which formed
  3. filtrationrecovered by filtration
  4. customRecrystallization of the crude product from CH2Cl2 /ethanol

Sources & evidence

ORD record
ord-1bde1444ca8d457495e8c0d8de371dcd
Source dataset
uspto-grants-1986_10
Patent number
US04616087

Reaction notes

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