Hydrochloric Acid → HCID 20231638, compound

HRID 371195Notes

Reaction equation

HRID 371195 reaction equation
CC([CH:5]([O:9][CH2:10][C:11]#[C:12][CH2:13][CH:14]([C:22]1[O:23][CH:24]=[CH:25][CH:26]=1)OC1CCCCO1)[C:6]([O-:8])=[O:7])(C)C.C1(=[O:32])CCC=C1.C(=O)([O-])[O-].[Na+].[Na+].C1(C=CC(O)=CC=1)O.Cl>>[OH:32][CH:25]1[CH2:26][C:22](=[O:23])[C:14]([CH2:13][C:12]#[C:11][CH2:10][O:9][CH2:5][C:6]([OH:8])=[O:7])=[CH:24]1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 785HydroquinoneHCID 10340Sodium CarbonateHCID 135882-Cyclopenten-1-oneHCID 131714263HCID 131714263, compound

Product 1

HCID 20231638HCID 20231638, compound

Procedure

The title compound is prepared by the method of Example 2 using 1 g of the title compound of Example 15, with the exception that the intermediate cyclopentenone is rearranged using aqueous sodium carbonate solution (pH 10-11) containing 1% hydroquinone. After stirring for 24 hours at room temperature, the reaction mixture is acidified to pH 2-3 with dilute hydrochloric acid and extracted with ether. The combined extracts are washed with brine, dried over sodium sulfate, filtered, and concentrated to dryness. The residue is chromatographed on Biosil A (using ethyl acetate/hexane is eluent) to afford the title compound. ##STR21##

Workup

  1. extractionextracted with ether
  2. washThe combined extracts are washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe residue is chromatographed on Biosil A (using ethyl acetate/hexane is eluent)

Sources & evidence

ORD record
ord-02f378d6e4644f8c970fe6a7b396c153
Source dataset
uspto-grants-1985_07
Patent number
US04529812

Reaction notes

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