Potassium Carbonate → HCID 86756175, compound

HRID 1387996Notes

Reaction equation

HRID 1387996 reaction equation
Br[C:2]1[S:6][C:5](/[CH:7]=[CH:8]/[C:9]([O:11][CH2:12]C)=[O:10])=[CH:4][CH:3]=1.B([O-])([O-])O[C:16]1[CH:21]=[CH:20][C:19]([CH:22]([CH3:24])[CH3:23])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O>[CH:22]([C:19]1[CH:20]=[CH:21][C:16]([C:2]2[S:6][C:5](/[CH:7]=[CH:8]/[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=2)=[CH:17][CH:18]=1)([CH3:24])[CH3:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15696497HCID 15696497, compoundHCID 86756176HCID 86756176, compound

Product 1

HCID 86756175HCID 86756175, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 86587398Ethanol toluene waterSolvent

Procedure

Under argon atmosphere, a solution of ethyl (E)-3-(5-bromothiophen-2-yl)acrylate (1.00 g), 4-isopropylphenyl borate (0.86 g) and potassium carbonate (1.12 g) in toluene/ethanol/water (40/4/4 ml) was stirred at room temperature for 1 hour. To the mixture was added tetrakistriphenylphosphine palladium (0.14 g), and the mixture was refluxed for 18 hours and then cooled to room temperature. The organic layer was washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the mixture was concentrated, and the residue was purified with column chromatography (ethyl acetate/hexane=1:9) to give pale yellow crystals of methyl (E)-3-[5-(4-isopropylphenyl)-thiophen-2-yl]acrylate (0.83 g).

Workup

  1. temperaturethe mixture was refluxed for 18 hours
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationUnder reduced pressure, the mixture was concentrated
  5. customthe residue was purified with column chromatography (ethyl acetate/hexane=1:9)

Sources & evidence

ORD record
ord-e296ae2f0df740b39a01d9fe18682c76
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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