Einecs 211-027-4 → 1-[5-Methoxy-2-(phenylethynyl)phenyl]-2-propanone

HRID 2291906Notes

Reaction equation

HRID 2291906 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].[Cl-].[NH+]1C=CC=C[CH:25]=1>CO>[CH3:25][O:13][C:10]1[CH:11]=[CH:12][C:7]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:8]([CH2:4][C:1](=[O:3])[CH3:2])[CH:9]=1

Participants

4

Reactant 2

HCID 69401Einecs 211-027-4HCID 143028923-Acetyl-3a,7a-dihydro-7a-(phenylethynyl)benzofuran-2,5(3H,4H)-dione

Product 1

HCID 140254751-[5-Methoxy-2-(phenylethynyl)phenyl]-2-propanoneYield 50.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Acetyl-3a,7a-dihydro-7a-(phenylethynyl)benzofuran-2,5(3H,4H)dione, (1.75 g 6 mmole), pyridinium chloride (1.5 g, 13 mmole) and MeOH (50 mL) were placed in a 100 mL round bottomed flask and heated at reflux for 2 hr. The solvent was removed under reduced pressure and the residue was partitioned between Et2O and water. The ether phase was washed with 3N hydrochloric acid, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was recrystallized from ethanol (10 mL) to give 0.8 g (50%) of the title compound as a light yellow solid, m.p. 63°-65° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hr
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was partitioned between Et2O and water
  5. washThe ether phase was washed with 3N hydrochloric acid
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was recrystallized from ethanol (10 mL)

Sources & evidence

ORD record
ord-695af3645d5b4e89999eab3f9a706c09
Source dataset
uspto-grants-1989_01
Patent number
US04798893

Reaction notes

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