3-(3,5-Dichloro-phenyl)-acrylic acid tert butyl ester → 3-(3,5-Dichlorophenyl)-propionic acid tert-butyl ester

HRID 1513289노트

반응식

HRID 1513289 반응식
[C:1]([O:5][C:6](=[O:17])[CH:7]=[CH:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([Cl:16])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pt]=O>[C:1]([O:5][C:6](=[O:17])[CH2:7][CH2:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([Cl:16])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 2

HCID 536582813-(3,5-Dichloro-phenyl)-acrylic acid tert butyl esterHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 669653423-(3,5-Dichlorophenyl)-propionic acid tert-butyl ester

시약·촉매·용매 2

HCID 82844Platinum oxide (PtO)촉매HCID 702Ethanol용매

실험 절차

3,5-dichloro-iodo-benzene (5 g, 18 mmol) was stirred at room temperature as a solution in DMF (50 mL) containing tert butyl acrylate (6.5 mL, 2.5 eq), tetrabutyl ammonium chloride hydrate (5.1 g, 1 eq), potassium acetate (5.4 g, 3 eq) and palladium (II) acetate (-200 mg, 30 mol %) for 5 hours. Reaction mixture was reduced in vacuo, partitioned between water and ethyl acetate. Ethyl acetate fractions were dried over magnesium sulfate, filtered over a small plug of silica gel. Silica gel plug washed with 10% Ethyl aceated/n-heptanes to afford 3-(3,5-Dichloro-phenyl)-acrylic acid tert butyl ester after evaporation as a white solid. 1H NMR (400 MHz, DMSO-D6) ppm 1.46 (s, 9H) 6.69 (d, J=16.04 Hz, 1 H) 7.49 (d, J=16.04 Hz, 1 H) 7.59 (t, J=1.89 Hz, 1 H) 7.81 (d, J=1.77 Hz, 2 H). A solution of 3-(3,5-Dichloro-phenyl)-acrylic acid tert butyl ester (4 g, 14 mmol) in ethanol (100 mL) was charged with platinum oxide (800 mg), after purging reaction mixture with nitrogen. Attached balloon of hydrogen and stirred vigorously at room temperature over night. After removal of excess hydrogen, catalyst was removed by filtering mixture over a pad of celite and the resulting solution was evaporated to afford 3-(3,5-dichloro-phenyl)-propionic acid tert-butyl ester as an oil (3.8 g; 94% isolated yield). 1H NMR (400 MHz, CHLOROFORM-D) ppm 1.41 (s, 9H) 2.52 (s, 2 H) 2.85 (s, 2 H) 7.08 (s, 2 H) 7.18 (s, 1 H).

후처리

  1. customafter evaporation as a white solid
  2. customafter purging
  3. customreaction mixture with nitrogen
  4. customAfter removal of excess hydrogen, catalyst
  5. customwas removed
  6. filtrationby filtering mixture over a pad of celite
  7. customthe resulting solution was evaporated
  8. customto afford

출처 및 근거

ORD 기록
ord-a76cde3d168148809d5eb7b62cd644ed
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08217065B2

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