Hydrochloric Acid → HCID 11558299, compound

HRID 884721Notes

Reaction equation

HRID 884721 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12](=[O:23])(=[O:22])[C:13]3[C:18]([C:19](=[O:21])[CH:20]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:7][CH:6]=1)(=O)C.C1COCC1.C([O-])([O-])=O.[K+].[K+].Cl>CO>[OH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12](=[O:23])(=[O:22])[C:13]3[C:18]([C:19](=[O:21])[CH:20]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 11522726HCID 11522726, compound

Product 1

HCID 11558299HCID 11558299, compoundYield 59.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(4-acetoxy-phenyl)-1,1-dioxo-1H-1λ6-thiochromen-4-one (260 mg, 0.79 mmol) in MeOH:THF (5 mL:5 mL), K2CO3 (133 mg, 0.95 mmol) was added and stirred for 2 h at rt Then the reaction mixture was neutralized by dilute HCl and extracted by EtOAc, the combined organic layer was washed with water, brine, dried and concentrated to give a crude product, which was purified by column chromatography using 50% EtOAc in hexane, to give 134 mg (59%) of 2-(4-hydroxy-phenyl)-1,1-dioxo-1H-1λ6-thiochromen-4-one. MS (ES) m/z: 286.05 (M), 285.01 (M−1); Mp. 222-224° C.

Workup

  1. extractionextracted by EtOAc
  2. washthe combined organic layer was washed with water, brine
  3. customdried
  4. concentrationconcentrated
  5. customto give a crude product, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-db35f0376cdc49a09548c686d834cbec
Source dataset
uspto-grants-2012_08
Patent number
US08242130B2

Reaction notes

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