HCID 19782188, compound → HCID 19782181, compound

HRID 258017Notes

Reaction equation

HRID 258017 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[CH:6]=[CH:5][C:4]=1[CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17]>C1(C)C=CC=CC=1.O.Cl.C(O)(=O)C.[Zn].[Hg](Cl)Cl>[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17]

Participants

8

Reactant 1

HCID 19782188HCID 19782188, compound

Product 1

HCID 19782181HCID 19782181, compound

Reagents, catalysts & solvents 6

HCID 23994ZincCatalystHCID 24085Mercuric ChlorideCatalystHCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent3×HCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

155.4 g of zinc turnings, 18.6 g of mercury(II) chloride, 231.2 ml of water and 7.7 ml of concentrated hydrochloric acid are combined and shaken well for 5 minutes. The aqueous phase is decanted off from the zinc amalgam and the latter is added to a solution of 78.45 g (0.31 mol) of the compound from Example 1 in 140 ml of toluene, 175 ml of water, 310 ml of concentrated hydrochloric acid and 15 ml of glacial acetic acid. The mixture is heated to reflux for 18 h, 81 ml of concentrated hydrochloric acid being added every 6 h. The solution is filtered, shaken 3 times with 300 ml of ethyl acetate each time and the combined ethyl acetate phases are washed with 500 ml of saturated sodium chloride solution. After drying over sodium sulphate, the solution is evaporated and the residue is flash chromatographed on silica gel using CH2Cl2 /acetone as the eluent.

Workup

  1. customThe aqueous phase is decanted off from the zinc amalgam
  2. temperatureThe mixture is heated
  3. temperatureto reflux for 18 h
  4. filtrationThe solution is filtered
  5. stirringshaken 3 times with 300 ml of ethyl acetate each time
  6. washthe combined ethyl acetate phases are washed with 500 ml of saturated sodium chloride solution
  7. dry with materialAfter drying over sodium sulphate
  8. customthe solution is evaporated
  9. customchromatographed on silica gel

Sources & evidence

ORD record
ord-ee4ceccbbb4d4012a64f6a43987c2ba2
Source dataset
uspto-grants-1993_11
Patent number
US05264458

Reaction notes

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