Methanol--water (1/1) → 2-Furan-3-yl-1-phenyl-ethanone

HRID 604478Notes

Reaction equation

HRID 604478 reaction equation
[C:1]1([C:7]2([CH2:13][C:14]3[CH:18]=[CH:17][O:16][CH:15]=3)SCCCS2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[OH:20].O>Cl[Hg]Cl>[O:16]1[CH:17]=[CH:18][C:14]([CH2:13][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:20])=[CH:15]1

Participants

4

Reactant 2

HCID 22242641Methanol--water (1/1)2×HCID 577096033-(2-Phenyl-[1,3]dithian-2-ylmethyl)-furan

Product 1

HCID 577096042-Furan-3-yl-1-phenyl-ethanone

Reagents, catalysts & solvents 1

HCID 24085Mercuric ChlorideCatalyst

Procedure

3-(2-Phenyl-[1,3]dithian-2-ylmethyl)-furan (11.5 g, 41 mmol) was suspended in 9:1 methanol/water (v/v) (150 mL) with slight heating. A solution of HgCl2 (22.3 g, 82 mmol) in methanol/water (50 mL) and solid HgO (8.0 g, 36.9 mmol) was added, and the mixture was heated at reflux under a nitrogen atmosphere for 6-7 h. The reaction mixture was filtered through celite to remove solids, and then concentrated. The resulting aqueous mixture was extracted with ethyl acetate, the combined organic extracts were washed with water, dried over sodium sulfate, and evaporated. The crude product was purified by flash column chromatography using 2% ethyl acetate in hexane as eluent. Yield: 5.7 g, 75%.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux under a nitrogen atmosphere for 6-7 h
  3. filtrationThe reaction mixture was filtered through celite
  4. customto remove solids
  5. concentrationconcentrated
  6. extractionThe resulting aqueous mixture was extracted with ethyl acetate
  7. washthe combined organic extracts were washed with water
  8. dry with materialdried over sodium sulfate
  9. customevaporated
  10. customThe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-511523c53da5411aa6242781f86b59db
Source dataset
uspto-grants-2011_03
Patent number
US07910613B2

Reaction notes

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