Hydrochloric Acid → HCID 22267254, compound

HRID 488878Notes

Reaction equation

HRID 488878 reaction equation
[O:1]=[C:2]1[C:11]([CH2:12][C:13]([O:15]CC)=[O:14])=[C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]2[C:4](=[CH:5][C:6]3[C:26](=[O:27])[O:25][CH2:24][C:7]=3[CH:8]=2)[O:3]1.Cl>C(O)(=O)C.C1COCC1.C(OCC)(=O)C>[O:1]=[C:2]1[C:11]([CH2:12][C:13]([OH:15])=[O:14])=[C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:9]2[C:4](=[CH:5][C:6]3[C:26](=[O:27])[O:25][CH2:24][C:7]=3[CH:8]=2)[O:3]1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 22267206HCID 22267206, compound

Product 1

HCID 22267254HCID 22267254, compoundYield 134.5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl 2-(2,8-dioxo-4-phenyl-6,8-dihydro-2H-furo[3,4-g]chromen-3-yl)acetate (58 mg) was dissolved in acetic acid (2 ml) and concentrated hydrochloric acid (1 ml), and heated under reflux for 30 minutes. The reaction solution was concentrated under reduced pressure to obtain the residue, which 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 chloride. After drying over magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was recrystallized from THF-isopropyl ether to obtain the title compound (72 mg, yield: 92%). Melting point: 226-227° C.

Workup

  1. temperatureunder reflux for 30 minutes
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. customto obtain the residue, which
  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 recrystallized from THF-isopropyl ether

Sources & evidence

ORD record
ord-be3b9626857d40049f309c8b054daa28
Source dataset
uspto-grants-2005_12
Patent number
US06974806B2

Reaction notes

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