Acetone → 1,5-Bis(2-fluorophenyl)penta-1,4-dien-3-one

HRID 77657Notes

Reaction equation

HRID 77657 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:10][C:11]([CH3:13])=[O:12].[OH-].[Na+].O>C(O)C>[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[CH:10][C:11](=[O:12])[CH:13]=[CH:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[F:1]

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 14798Sodium HydroxideHCID 67970o-Fluorobenzaldehyde

Product 1

HCID 42564721,5-Bis(2-fluorophenyl)penta-1,4-dien-3-oneYield 42.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Fluorobenzaldehyde (1t, 0.5 ml, 4.7 mmol) and acetone (19, 0.18 ml, 2.4 mmol) were combined in ethanol (20 ml) and stirred for 10 min at room temperature. A solution of sodium hydroxide (0.29 g, 7.3 mmol) and water (15 ml) was added and the mixture stirred for 18 hr at room temperature. The resulting mixture was filtered and chromatographed on silica gel with ethyl acetate/hexane to give a solid. The crude solid was recrystallized from ethanol to afford 0.27 g (41%) of yellow crystals: mp 68-72° C. [expected mp 68-70° C.]; 1H NMR: δ 7.13 (m, 6H), 7.36 (m, 2H), 7.61 (dt, 2H, J=7.6 Hz, 1.4 Hz), 7.84 (d, 2H, J=16.3 Hz); 13C NMR: δ 116.2, 122.8, 124.4, 127.6, 129.3, 131.8, 135.9, 161.5, 188.7.

Workup

  1. stirringthe mixture stirred for 18 hr at room temperature
  2. filtrationThe resulting mixture was filtered
  3. customchromatographed on silica gel with ethyl acetate/hexane
  4. customto give a solid
  5. customThe crude solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-19da917bc677416abc1689a490cd72ec
Source dataset
uspto-grants-2014_09
Patent number
US08841326B2

Reaction notes

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