Hydrochloric Acid → HCID 22267274, compound

HRID 488867Notes

Reaction equation

HRID 488867 reaction equation
C([O:3][C:4](=[O:27])[CH2:5][C:6]1[C:7](=[O:26])[O:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:13][C:12]1[CH2:22][CH2:23][C:24](=[O:25])[C:11]=1[CH:10]=2)C.Cl>C(O)(=O)C>[O:26]=[C:7]1[C:6]([CH2:5][C:4]([OH:27])=[O:3])=[C:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:14]2[C:9](=[CH:10][C:11]3[C:24](=[O:25])[CH2:23][CH2:22][C:12]=3[CH:13]=2)[O:8]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23405761HCID 23405761, compound

Product 1

HCID 22267274HCID 22267274, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Ethyl(2,8-dioxo-4-phenyl-2,6,7,8-tetrahydrocyclopenta[g]chromen-3-yl)acetate (1.2 g) was dissolved in acetic acid (20 ml) and concentrated hydrochloric acid (10 ml), and heated under reflux for 30 minutes. The reaction solution was concentrated under reduced pressure, and the resultant residue was dissolved in a solvent mixture of THF (10 ml) and ethyl acetate (50 ml), and then washed with water followed by a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride. After drying over magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by recrystallization from ethyl acetate to obtain the title compound (0.87 g, yield: 79%).

Workup

  1. temperatureunder reflux for 30 minutes
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. dissolutionthe resultant residue was dissolved in a solvent mixture of THF (10 ml) and ethyl acetate (50 ml)
  4. washwashed with water
  5. dry with materialAfter drying over magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe residue was purified by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-d071cb469aa04502b1338418d8c523c3
Source dataset
uspto-grants-2005_12
Patent number
US06974806B2

Reaction notes

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