Potassium Carbonate → Ethyl 2-methyl-2-[2-methyl-4-[3-(3-methylbenzothiophen-2-yl)propionyl]phenoxy]propionate

HRID 241362Notes

Reaction equation

HRID 241362 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:21])[CH2:9][CH2:10][C:11]2[S:12][C:13]3[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=3[C:15]=2[CH3:16])=[CH:4][C:3]=1[CH3:22].C(=O)([O-])[O-].[K+].[K+].Br[C:30]([CH3:37])([CH3:36])[C:31]([O:33][CH2:34][CH3:35])=[O:32].[Cl-].[NH4+]>CC(=O)CC>[CH3:36][C:30]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:21])[CH2:9][CH2:10][C:11]2[S:12][C:13]3[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=3[C:15]=2[CH3:16])=[CH:4][C:3]=1[CH3:22])([CH3:37])[C:31]([O:33][CH2:34][CH3:35])=[O:32]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 25517Ammonium ChlorideHCID 668845751-(4-Hydroxy-3-methylphenyl)-3-(3-methylbenzothiophen-2-yl)propan-1-one

Product 1

HCID 66884301Ethyl 2-methyl-2-[2-methyl-4-[3-(3-methylbenzothiophen-2-yl)propionyl]phenoxy]propionateYield 72.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To an ice-cold suspension of 1-(4-hydroxy-3-methylphenyl)-3-(3-methylbenzothiophen-2-yl)propan-1-one [Example 1 (1)] (200 mg, 0.645 mmol) and potassium carbonate (445 mg, 3.22 mmol) in 2-butanone (6.4 mL) was added slowly ethyl 2-bromo-2-methylpropionate (0.48 mL, 3.2 mmol). The mixture was heated under reflux for 20 hours, to which was added saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/1), to give the titled compound as a pale yellow oil (198 mg, yield 72%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 20 hours, to which
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/1)

Sources & evidence

ORD record
ord-c2748a13cdc1488680a4ae5f14dd65f8
Source dataset
uspto-grants-2014_02
Patent number
US08648208B2

Reaction notes

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