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

HRID 2228212
Notes
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Reaction equation

HRID 2228212 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 178418397
HCID 178418397, compound
Catalyst
HCID 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-27b72d26eb6549a58d2a7479970951b0
Source dataset
uspto-grants-2002_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06413947B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes