Sulfuric Acid → Ethanone, 1-(3-ethyl-4-fluorophenyl)-

HRID 2415258Notes

Reaction equation

HRID 2415258 reaction equation
OS(O)(=O)=O.[CH2:6]([C:8]1[CH:9]=[C:10]([C:15]#[C:16][Si](C)(C)C)[CH:11]=[CH:12][C:13]=1[F:14])[CH3:7].[O:21]1CCCC1>O.[Hg]=O>[CH2:6]([C:8]1[CH:9]=[C:10]([C:15](=[O:21])[CH3:16])[CH:11]=[CH:12][C:13]=1[F:14])[CH3:7]

Participants

6

Reactant 3

HCID 1118Sulfuric Acid2×HCID 8028TetrahydrofuranHCID 226410492-Ethyl-1-fluoro-4-[2-(trimethylsilyl)ethynyl]benzene

Product 1

HCID 22641004Ethanone, 1-(3-ethyl-4-fluorophenyl)-

Reagents, catalysts & solvents 2

HCID 30856Mercuric oxideCatalystHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of H2SO4 (0.25 mL) in H2O (3 mL), HgO (154 mg, 0.712 mmol) was added. Another portion of H2SO4 (0.5 mL) was added so that all of the mercury oxide dissolved. Then the mixture was warmed to 60° C. and (3-ethyl-4-fluoro-phenylethynyl)-trimethyl-silane (1.57 g, 7.12 mmol) was added with tetrahydrofuran (2 mL) during 20 minutes. After the addition, the mixture was stirred for an additional 30 minutes and then cooled and extracted with ether. The extract was passed through a celite pad, washed with saturated brine and dried (Na2SO4). Removal of solvent on a rotary evaporator gave a brown oil, which was chromatographed (25%, dichloromethane/hexanes) to give a yellow oil. 404 mg, 34%.

Workup

  1. dissolutiondissolved
  2. additionAfter the addition
  3. temperaturecooled
  4. extractionextracted with ether
  5. washwashed with saturated brine
  6. dry with materialdried (Na2SO4)
  7. customRemoval of solvent
  8. customon a rotary evaporator
  9. customgave a brown oil, which
  10. customwas chromatographed (25%, dichloromethane/hexanes)
  11. customto give a yellow oil

Sources & evidence

ORD record
ord-d58441af837240a58e709886010dab0c
Source dataset
uspto-grants-2004_11
Patent number
US06818663B2

Reaction notes

Loading…