Cyclopropyl methyl ketone → HCID 54225680, compound

HRID 2295236Notes

Reaction equation

HRID 2295236 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]([CH:13]1[CH2:15][CH2:14]1)=[O:12].[O-]CC.[Na+]>C(O)C>[CH:13]1([C:11](=[O:12])[CH:10]=[CH:6][C:5]2[CH:8]=[CH:9][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 13004Cyclopropyl methyl ketoneHCID 680234-Fluorobenzaldehyde2×HCID 2723922Sodium ethoxide

Product 1

HCID 54225680HCID 54225680, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 4-fluorobenzaldehyde (9.30 g, 75.00 mmol, Aldrich) and cyclopropyl methyl ketone (6.30 g, 75.00 mmol) in absolute ethanol (100 ml) was treated with a solution of sodium ethoxide in ethanol (21% by weight solution; 2.79 ml, 7.50 mmol). After stirring for 2 hours at room temperature, additional 4-fluorobenzaldehyde was added (1.86 g, 15.00 mmol). The reaction mixture was stirred for 2 hours, concentrated to 1/3 volume and partitioned between 50% saturated NH4Ct/EtOAc (100 ml/250 ml). The layers were separated and the aqueous portion was extracted with EtOAc (twice) and the combined organics were washed with H2O (twice) and brine, dried (Na2SO4) and concentrated. The yellow oily residue was distilled (Vigroux column, bp 115°-120° C., 0.6 mm Hg) to afford the title compound as a colorless oil (12.8 g, 89.7%).

Workup

  1. stirringThe reaction mixture was stirred for 2 hours
  2. concentrationconcentrated to 1/3 volume
  3. custompartitioned between 50% saturated NH4Ct/EtOAc (100 ml/250 ml)
  4. customThe layers were separated
  5. extractionthe aqueous portion was extracted with EtOAc (twice) and the combined
  6. washorganics were washed with H2O (twice) and brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. distillationThe yellow oily residue was distilled (Vigroux column, bp 115°-120° C., 0.6 mm Hg)

Sources & evidence

ORD record
ord-46e54e2d35d645f790670a284044e54d
Source dataset
uspto-grants-1997_11
Patent number
US05691322

Reaction notes

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