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

HRID 566017노트

반응식

HRID 566017 반응식
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

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 66602552Toluene-ethanol water용매

실험 절차

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 5days. 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.

후처리

  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

출처 및 근거

ORD 기록
ord-a66316c099734df8a182fadaba888a58
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06172061B2

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