Potassium Carbonate → methyl (E)-3-[4-(4-methylphenyl)thiophen-2-yl)acrylate

HRID 566022Notes

Reaction equation

HRID 566022 reaction equation
C/[C:2](=[CH:6]\[C:7]1[S:8][CH:9]=[C:10](Br)[CH:11]=1)/[C:3]([OH:5])=[O:4].B([O-])([O-])O[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1.[C:24](=O)([O-])[O-].[K+].[K+]>C1(C)C(CCO)=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:21][C:18]1[CH:19]=[CH:20][C:15]([C:10]2[CH:11]=[C:7](/[CH:6]=[CH:2]/[C:3]([O:5][CH3:24])=[O:4])[S:8][CH:9]=2)=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 866453334-Methylphenyl borateHCID 86756172methyl (E)-3-(4-bromothiophen-2-yl)acrylic acid

Product 1

HCID 86756171methyl (E)-3-[4-(4-methylphenyl)thiophen-2-yl)acrylateYield 76.5%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 66602552Toluene-ethanol waterSolvent

Procedure

Under argon atmosphere, a solution of methyl (E)-3-(4-bromothiophen-2-yl)acrylic acid (3.0 g), 4-methylphenyl borate (1.82 g) and potassium carbonate (3.36 g) in toluene-ethanol-water (120-12-12 ml) was stirred at room temperature for 1 hour. To the reaction mixture was added tetrakistriphenylphosphinepalladium (0.42 g), and the mixture was refluxed for 24 hours and cooled to room temperature. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate/hexane=1:9→1:5→1:2) to give methyl (E)-3-[4-(4-methylphenyl)thiophen-2-yl)acrylate (2.40 g) as pale yellow crystals.

Workup

  1. temperaturethe mixture was refluxed for 24 hours
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified with column chromatography (ethyl acetate/hexane=1:9→1:5→1:2)

Sources & evidence

ORD record
ord-9488d397c6af4c089891a9a14d1ee4ff
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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