Hydrochloric Acid → HCID 20231638, compound

HRID 2290666Notes

Reaction equation

HRID 2290666 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 commpound 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 as 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 as eluent)

Sources & evidence

ORD record
ord-1a8dd31998a04564853610c998dcf6b2
Source dataset
uspto-grants-1986_10
Patent number
US04617411

Reaction notes

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