Acetone → 1,5-Bis(3-fluorophenyl)-1,4-pentadien-3-one

HRID 714171Notes

Reaction equation

HRID 714171 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[CH3:10][C:11]([CH3:13])=[O:12].[OH-].[Na+].O>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:10][C:11](=[O:12])[CH:13]=[CH:5][C:4]2[CH:7]=[CH:8][CH:9]=[C:2]([F:1])[CH:3]=2)[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 14798Sodium HydroxideHCID 680093-Fluorobenzaldehyde

Product 1

HCID 695017221,5-Bis(3-fluorophenyl)-1,4-pentadien-3-oneYield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Fluorobenzaldehyde (1s, 0.5 ml, 4.7 mmol) and acetone (19, 0.18 ml, 2.3 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 was recrystallized from ethanol to afford 0.26 g (42%) of yellow crystals: mp 96-97° C. [expected mp 96-97° C.]; 1H NMR: δ 7.03 (d, 2H, J=16.1 Hz), 7.09 (m, 2H), 7.35 (m, 6H), 7.67 (d, 2H, J=15.9 Hz); 13C NMR: δ 114.4, 117.5, 124.4, 126.3, 130.4, 136.9, 142.0, 162.9, 188.1; Anal. Calcd for C17H12OF2: C, 75.55; H, 4.48. Found: C, 75.26; H, 4.65.

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 was recrystallized from ethanol

Sources & evidence

ORD record
ord-6ac76e8e1e11405c82345397eaae86a8
Source dataset
uspto-grants-2015_11
Patent number
US09187397B2

Reaction notes

Loading…