Ethyl bromoacetate → Ethyl 2-methyl-4-[3-(3-methylbenzothiophen-2-yl)propionyl]phenoxyacetate

HRID 241360Notes

Reaction equation

HRID 241360 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[CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32].[Cl-].[NH4+]>CC(C)=O>[CH3:22][C:3]1[CH:4]=[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:6]=[CH:7][C:2]=1[O:1][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 668845751-(4-Hydroxy-3-methylphenyl)-3-(3-methylbenzothiophen-2-yl)propan-1-one

Product 1

HCID 66884017Ethyl 2-methyl-4-[3-(3-methylbenzothiophen-2-yl)propionyl]phenoxyacetateYield 87.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To an ice-cold suspension of the above-mentioned 1-(4-hydroxy-3-methylphenyl)-3-(3-methylbenzothiophen-2-yl)propan-1-one (200 mg, 0.644 mmol) and potassium carbonate (178 mg, 1.29 mmol) in acetone (6.4 mL) was added slowly ethyl bromoacetate (0.14 mL, 1.3 mmol). The mixture was heated under reflux for 3 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=5/1), to give the titled compound as a colorless oil (223 mg, yield 87%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 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=5/1)

Sources & evidence

ORD record
ord-b562fb30a3474a38b3570b3e49ae4408
Source dataset
uspto-grants-2014_02
Patent number
US08648208B2

Reaction notes

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