Potassium Carbonate → 1-[5-Hydroxy-2-(phenylethynyl)phenyl]-2-propanone

HRID 2291902Notes

Reaction equation

HRID 2291902 reaction equation
[C:1]([CH:4]1[CH:8]2[CH2:9][C:10](=[O:13])[CH:11]=[CH:12][C:7]2([C:14]#[C:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)OC1=O)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO.O>[OH:13][C:10]1[CH:11]=[CH:12][C:7]([C:14]#[C:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[C:8]([CH2:4][C:1](=[O:3])[CH3:2])[CH:9]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 143028923-Acetyl-3a,7a-dihydro-7a-(phenylethynyl)benzofuran-2,5(3H,4H)-dione

Product 1

HCID 212782891-[5-Hydroxy-2-(phenylethynyl)phenyl]-2-propanoneYield 65%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3-Acetyl-3a,7a-dihydro-7a-(phenylethynyl)benzofuran-2,5-(3H,4H)-dione, the product of Example 1A, (1.5 g, 5 mmole) was dissolved in MeOH (50 mL) and water (10 mL). Anhydrous potassium carbonate 7.1 g, 50 mmole) was added and the mixture was heated at reflux for 45 min. The reaction was quenched into ice cold 3N hydrochloric acid and extracted with EtOAc (3×50 mL). The combined extracts were washed with water (50 mL) and brine (2×50 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by flash column chromatography (silica gel; 3:1::hexane:EtOAc) to give 0.84 g (65%) of the title compound as a light brown crystalline solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 45 min
  3. customThe reaction was quenched into ice cold 3N hydrochloric acid
  4. extractionextracted with EtOAc (3×50 mL)
  5. washThe combined extracts were washed with water (50 mL) and brine (2×50 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash column chromatography (silica gel; 3:1::hexane:EtOAc)

Sources & evidence

ORD record
ord-376a0cdeb65c43278520ee35b137fe6d
Source dataset
uspto-grants-1989_01
Patent number
US04798893

Reaction notes

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