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

HRID 2228207ノート

反応式

HRID 2228207 の反応式
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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 66602552Toluene-ethanol water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-22677af573d64d63af03b167c7cabf6e
出典データセット
uspto-grants-2002_07
特許番号
US06413947B1

反応ノート

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