Acetophenone → 1-(4-Fluoro-3-methyl-phenyl)-3-phenyl-1,3-propanedione

HRID 68557Notes

Reaction equation

HRID 68557 reaction equation
CC([O-])(C)C.[K+].[C:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:9])[CH3:8].C[O:17][C:18](=O)[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[C:21]([CH3:26])[CH:20]=1>C1COCC1>[F:25][C:22]1[CH:23]=[CH:24][C:19]([C:18](=[O:17])[CH2:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:9])=[CH:20][C:21]=1[CH3:26]

Participants

5

Reactant 3

HCID 7410AcetophenoneHCID 18788764Methyl 4-fluoro-3-methylbenzoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 821204491-(4-Fluoro-3-methyl-phenyl)-3-phenyl-1,3-propanedione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

17.3 g KOtBu was dissolved in 500 mL THF and 9 mL acetophenone was added. After 15 min at RT 25.9 g 4-fluoro-3-methyl-benzoic acid methyl ester was added and stirred for 3 h at RT. The solvent was removed and the residue was purified by chromatography on silica gel (cyclohexane/EE: 98:2) to yielded 19.3 g of the desired compound.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by chromatography on silica gel (cyclohexane/EE: 98:2)

Sources & evidence

ORD record
ord-1e25565a25144251bb4ccb2e655ee1af
Source dataset
uspto-grants-2014_09
Patent number
US08822464B2

Reaction notes

Loading…