Potassium Carbonate → Trifluoromethanesulfonic Acid 4-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenyl Ester

HRID 546856Notes

Reaction equation

HRID 546856 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][C:8]([C:11]([CH2:13]Cl)=[O:12])([CH3:10])[CH3:9].[CH2:15]([C:17]([C:28]1[CH:33]=[CH:32][C:31]([O:34][S:35]([C:38]([F:41])([F:40])[F:39])(=[O:37])=[O:36])=[C:30]([CH3:42])[CH:29]=1)([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([CH3:27])[CH:21]=1)[CH2:18][CH3:19])[CH3:16]>CC(C)=O>[CH3:7][C:8]([CH3:10])([CH3:9])[C:11](=[O:12])[CH2:13][O:26][C:23]1[CH:24]=[CH:25][C:20]([C:17]([C:28]2[CH:33]=[CH:32][C:31]([O:34][S:35]([C:38]([F:41])([F:39])[F:40])(=[O:37])=[O:36])=[C:30]([CH3:42])[CH:29]=2)([CH2:18][CH3:19])[CH2:15][CH3:16])=[CH:21][C:22]=1[CH3:27]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 835721-ChloropinacoloneHCID 58598300Trifluoromethanesulfonic acid 4-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenyl ester

Product 1

HCID 11203079Trifluoromethanesulfonic Acid 4-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenyl EsterYield 83.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (59.7 mg, 0.43 mmol) and 1-chloropinacolin (42.0 mg, 0.31 mmol) were added to a solution of trifluoromethanesulfonic acid 4-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenyl ester (Example 1-(1); 0.1 g, 0.24 mmol) in acetone (1.2 mL), and the mixture was heated under reflux for 17 hours. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (6% ethyl acetate/hexane) to give the title compound (103.5 mg, 83%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 17 hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (6% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-3d6b5120bd8646c6927074c7a85dd9dd
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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