N-Iodosuccinimide → (E)-ethyl 3-(4-iodophenyl)acrylate

HRID 1057183노트

반응식

HRID 1057183 반응식
[I:1]N1C(=O)CCC1=O.[CH2:9]([O:11][C:12](=[O:24])/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)[CH3:10]>CC#N.CCOC(C)=O>[I:1][C:18]1[CH:19]=[CH:20][C:15](/[CH:14]=[CH:13]/[C:12]([O:11][CH2:9][CH3:10])=[O:24])=[CH:16][CH:17]=1

참가 물질

5

반응물 2

HCID 120273N-IodosuccinimideHCID 59425074-(E-3-Ethoxy-3-oxo-1-propen-1-yl)benzeneboronic acid

생성물 1

HCID 21107276(E)-ethyl 3-(4-iodophenyl)acrylate수율 86.1%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

N-Iodosuccinimide (2.5 g, 11 mmol) was added to a suspension of 4-(E-3-ethoxy-3-oxo-1-propen-1-yl)phenylboronic acid (2.2 g, 10 mmol) in CH3CN (50 mL) at room temperature. The reaction was covered with foil, stirred for 26 h, and then diluted with EtOAc. The resulting mixture was washed with water (2×100 mL), washed with sodium thiosulfate (100 mL), dried (MgSO4), filtered, and concentrated. The crude material was purified by silica gel chromatography (0-50% EtOAc in hexanes) to give 2.6 g of (E)-ethyl 3-(4-iodophenyl)acrylate as a yellow oil. 1H NMR (400 MHz, DMSO-d6): δ 7.79 (d, 2H), 7.60 (d, 1H), 7.53 (d, 2H), 6.68 (d, 1H), 4.19 (q, 2H), 1.26 (t, 3H); LCMS: 303 (M+H)+.

후처리

  1. washThe resulting mixture was washed with water (2×100 mL)
  2. washwashed with sodium thiosulfate (100 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by silica gel chromatography (0-50% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-80fed62a93c8441ca1baaa323d5d139b
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09399646B2

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