Hydrochloric Acid → HCID 70358548, compound

HRID 649528Notes

Reaction equation

HRID 649528 reaction equation
C[O:2][C:3]1[C:9]2[S:10][CH:11]=[CH:12][C:8]=2[C:7](=[CH:13][C:14]([OH:16])=[O:15])[C:6]2[CH:17]=[CH:18][CH:19]=[CH:20][C:5]=2[CH:4]=1.Cl>O1CCCC1>[OH:2][C:3]1[C:9]2[S:10][CH:11]=[CH:12][C:8]=2[C:7](=[CH:13][C:14]([OH:16])=[O:15])[C:6]2[CH:17]=[CH:18][CH:19]=[CH:20][C:5]=2[CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 3035543HCID 3035543, compound

Product 1

HCID 70358548HCID 70358548, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 g of the cis isomer product of example 5 is dissolved in tetrahydrofuran and 1N HCl is then added until the solution becomes turbid. The reaction mixture is refluxed for 2.5 hours and the organic solvent then evaporated off under reduced pressure. The remaining aqueous phase is extracted with ethyl acetate and the organic phase separated, washed with brine, dried over MgSO4 and evaporated under reduced pressure. The residue is recrystallised from dichloromethane/hexane to yield the title compound in the form of the pure (Z) isomer: M.P.=203°-208° C.

Workup

  1. temperatureThe reaction mixture is refluxed for 2.5 hours
  2. customthe organic solvent then evaporated off under reduced pressure
  3. extractionThe remaining aqueous phase is extracted with ethyl acetate
  4. customthe organic phase separated
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated under reduced pressure
  8. customThe residue is recrystallised from dichloromethane/hexane

Sources & evidence

ORD record
ord-dfdd805f1a3c4bd28509b2c3cccb6a40
Source dataset
uspto-grants-1988_04
Patent number
US04740518

Reaction notes

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