Water → HCID 59541970, compound

HRID 1893237Notes

Reaction equation

HRID 1893237 reaction equation
O[C:2]1([C:9]2[CH:14]=[CH:13][CH:12]=[C:11](SC)[CH:10]=2)[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.[CH3:17]C[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC.O.O[O:34][S:35]([O-:37])=O.[K+]>C1COCC1.CO>[CH3:17][S:35]([C:11]1[CH:10]=[C:9]([C:2]2[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH:3]=2)[CH:14]=[CH:13][CH:12]=1)(=[O:37])=[O:34]

Participants

7

Reactant 4

HCID 962WaterHCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 23707502Potassium hydroxy sulfiteHCID 59541959HCID 59541959, compound

Product 1

HCID 59541970HCID 59541970, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-hydroxy-4-(3-methylsulfanyl-phenyl)-cyclohexanone (as prepared in the previous step, 1.10 g, 4.66 mmol) in THF (10 mL) was treated with Burgess' reagent (1.20 g, 5.00 mmol) at room temperature overnight. The solvent was removed and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered, concentrated to give a white solid. To this white solid in MeOH (5 mL) and water (5 mL) was added OXONE (Aldrich, 6.10 g, 10 mmol) at room temperature. The reaction mixture was stirred overnight and quenched with saturated NaHCO3. The solvent was removed in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered, concentrated and purified by silica gel column on a CombiFlash® system using hexanes and ethyl acetate (from 10% ethyl acetate to 100% ethyl acetate) to afford the title compound as a white solid.

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a white solid
  8. customquenched with saturated NaHCO3
  9. customThe solvent was removed in vacuo
  10. customthe residue was partitioned between ethyl acetate and water
  11. washThe organic layer was washed with brine
  12. dry with materialdried over anhydrous Na2SO4
  13. filtrationfiltered
  14. concentrationconcentrated
  15. custompurified by silica gel column on a CombiFlash® system

Sources & evidence

ORD record
ord-75f733aa99dc45a7890b6cefaf5a4347
Source dataset
uspto-grants-2013_08
Patent number
US08513229B2

Reaction notes

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