Potassium Carbonate → (E)-3-[5-(4-methylphenyl)-thiophen-2-yl]acrylic acid

HRID 1387946Notes

Reaction equation

HRID 1387946 reaction equation
Br[C:2]1[S:6][C:5](/[CH:7]=[CH:8]/[C:9]([O:11]C)=[O:10])=[CH:4][CH:3]=1.B([O-])([O-])O[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>C1(C)C(CCO)=CC=CC=1.O.O1CCCC1.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.O>[CH3:21][C:18]1[CH:19]=[CH:20][C:15]([C:2]2[S:6][C:5](/[CH:7]=[CH:8]/[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=2)=[CH:16][CH:17]=1

Participants

9

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 25417100(E)-methyl 3-(5-bromothiophen-2-yl)acrylateHCID 866453334-Methylphenyl borate

Product 1

HCID 11345563(E)-3-[5-(4-methylphenyl)-thiophen-2-yl]acrylic acidYield 48%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 66602552Toluene-ethanol waterSolvent

Procedure

Under argon atmosphere, a solution of methyl (E)-3-(5-bromothiophen-2-yl)acrylate (4.0 g), 4-methylphenyl borate (2.64 g) and potassium carbonate (4.48 g) in toluene-ethanol-water (160-16-16 ml) was stirred at room temperature for 1 hour. To the reaction mixture was added tetrakistriphenylphosphinepalladium (0.56 g), and the mixture was refluxed for 16 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 to give crude product (5.24 g). To a solution of the resulting carboxylic acid ester (5.24 g) in tetrahydrofuran (100 ml) was added 1N sodium hydroxide (20 ml) at room temperature, and the mixture was stirred for 5 days. To the reaction mixture was added water, and the mixture was washed with ethyl acetate. The aqueous layer was acidified with concentrated hydrochloric acid, and the mixture was extracted with ethyl acetate, washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure to give (E)-3-[5-(4-methylphenyl)-thiophen-2-yl]acrylic acid (1.9 g) as yellow crystals.

Workup

  1. temperaturethe mixture was refluxed for 16 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. customto give crude product (5.24 g)
  6. washthe mixture was washed with ethyl acetate
  7. extractionthe mixture was extracted with ethyl acetate
  8. washwashed with saturated sodium chloride solution
  9. dry with materialdried with magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-905f4c8eae7d44d2a5882065ff0c7174
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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