Potassium Carbonate → HCID 58237458, compound

HRID 885258Notes

Reaction equation

HRID 885258 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.F[C:14]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:15]=1[CH:16]=[O:17].C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[CH:16]([C:15]1[CH:18]=[C:19]([C:22]([F:23])([F:24])[F:25])[CH:20]=[CH:21][C:14]=1[O:1][C:2]1[CH:3]=[C:4]([CH:8]([CH3:12])[C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1)=[O:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27349042-Fluoro-5-(trifluoromethyl)benzaldehydeHCID 124468532-(3-Hydroxyphenyl)propionic acid, (+-)-

Product 1

HCID 58237458HCID 58237458, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

2-(3-Hydroxy-phenyl)-propionic acid (0.1 g, 0.60 mmol), 2-fluoro-5-(trifluoromethyl)benzaldehyde (0.115 g, 0.60 mmol), and potassium carbonate (0.165 g, 1.19 mmol) were combined in THF and stirred at 70° C. overnight. The mixture was partitioned between H2O and EtOAc and acidified with 1N aqueous HCl to pH 1, and then extracted with EtOAc. The combined organic layers were dried over MgSO4, filtered, and concentrated, and residue was purified by silica gel chromatography to give the desired product.

Workup

  1. customThe mixture was partitioned between H2O and EtOAc
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customresidue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-fbe79f76a0b0423c807fca4ae14d025f
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

Loading…