Hydrochloric Acid → 4-[2-(Ethoxycarbonyl)vinyl]phenylacetic Acid

HRID 1166570노트

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HRID 1166570 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[C:12]([O:16][CH2:17][CH3:18])(=[O:15])[CH:13]=[CH2:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(C(C)C)CC)(C)C.Cl>CN(C)C=O.C([O-])(=O)C.C([O-])(=O)C.[Pd+2].C(OCC)(=O)C>[CH2:17]([O:16][C:12]([CH:13]=[CH:14][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1)=[O:15])[CH3:18]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 8821Ethyl AcrylateHCID 11776TriphenylphosphineHCID 74654Benzeneacetic acid, 4-bromo-HCID 81531Diisopropylethylamine

생성물 1

HCID 696934804-[2-(Ethoxycarbonyl)vinyl]phenylacetic Acid

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

To a stirred solution of 4-bromophenylacetic acid (43.0 g, 200 mmol) in dimethyl formamide (400 mL) in a round bottom flask under nitrogen atmosphere at room temperature was added ethyl acrylate (43.3 mL, 400 mmol), palladium diacetate (0.90 g, 4 mmol), triphenylphosphine (2.10 g, 8 mmol), and diisopropylethylamine (87.2 mL, 500 mmol). The reaction mixture was heated to 100° C. for 43 hours, cooled to room temperature, and hydrochloric acid (1N, 1 L) was added. To the reaction mixture was added ethyl acetate (500 mL), the aqueous layer was extracted with ethyl acetate (2×500 mL), and the combined organic layers washed with hydrochloric acid (1N, 500 mL), water (500 mL) and saturated sodium chloride solution (250 mL), then dried over sodium sulfate, filtered and evaporated in vacuo to provide the title compound as a mixture of cis and trans isomers (46.9 g, 100%).

후처리

  1. temperaturecooled to room temperature
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×500 mL)
  3. washthe combined organic layers washed with hydrochloric acid (1N, 500 mL), water (500 mL) and saturated sodium chloride solution (250 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-ae3a27a6a14e4911884c7cdd1a995f47
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06613911B2

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