Pinacolone → HCID 54149056, compound

HRID 2293867Notes

Reaction equation

HRID 2293867 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13].[O-]CC.[Na+]>C(O)C>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6416PinacoloneHCID 680234-FluorobenzaldehydeHCID 2723922Sodium ethoxide

Product 1

HCID 54149056HCID 54149056, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 4-fluorobenzaldehyde (12.13 ml, 110 mmol, Aldrich) and pinacolone (12.48 ml, 100 mmol, Aldrich) in absolute ethanol (120 ml) was treated with a solution of sodium ethoxide in ethanol (21% by weight solution; 3.72 ml, 10 mmol). The clear yellow reaction mixture was stirred at room temperature under argon for 24 hours. The reaction mixture was concentrated to 1/3 volume and partitioned between 50% saturated NH4 Cl and EtOAc. The layers were separated and the organic layer was washed twice with H2O and brine then dried (Na2SO4) and concentrated under reduced pressure. The oily residue was purified by flash chromatography (Merck Silica gel, 10% EtOAc/hexane), yielding the title compound as a colorless oil that slowly solidified. The white solid was recrystallized from hexane, yielding the title compound as white crystals (13.9 g, 67.5%).

Workup

  1. concentrationThe reaction mixture was concentrated to 1/3 volume
  2. custompartitioned between 50% saturated NH4 Cl and EtOAc
  3. customThe layers were separated
  4. washthe organic layer was washed twice with H2O and brine
  5. dry with materialthen dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe oily residue was purified by flash chromatography (Merck Silica gel, 10% EtOAc/hexane)

Sources & evidence

ORD record
ord-9d6640401f244e7481e2f02be61c0a95
Source dataset
uspto-grants-1997_11
Patent number
US05686433

Reaction notes

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