Acetic Acid → HCID 10264769, compound

HRID 1727272Notes

Reaction equation

HRID 1727272 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[C:7]3[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:8]3=[CH:9][CH:10]=2)[O:5][C:4](=[O:17])[CH:3]=1.CC(O)=O.Cl[CH2:23][C:24](=O)[CH3:25]>C1(C)C=CC=CC=1.CCO.O>[CH3:16][C:12]1[C:8]2[CH:9]=[CH:10][C:11]3[C:2]4[O:1][CH:23]=[C:24]([CH3:25])[C:3]=4[C:4](=[O:17])[O:5][C:6]=3[C:7]=2[CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 6571ChloroacetoneHCID 547180894-Hydroxy-7-methyl-benzo[h]chromen-2-one

Product 1

HCID 10264769HCID 10264769, compoundYield 60.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of 7 (50 mg, 0.22 mmol) in toluene (8 mL) was added a mixture of HOAc (66 mg, 1.1 mmol) and NH4OAc (80 mg, 1.1 mmol) in EtOH (2 mL) and chloroacetone (103 mg, 1.1 mmol). The mixture was refluxed 24 h. After cooling, the mixture was diluted with H2O and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered, and evaporated. The residue was purified by column chromatography to give 1 (35 mg, 60%) as a white solid. The spectroscopic data of synthetic compound 1 were identical with those of the natural product 1.

Workup

  1. temperatureThe mixture was refluxed 24 h
  2. temperatureAfter cooling
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-5233c3031ff54be198abe5fa827bbe38
Source dataset
uspto-grants-2009_02
Patent number
US07495026B2

Reaction notes

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