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

HRID 1057183ノート

反応式

HRID 1057183 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-80fed62a93c8441ca1baaa323d5d139b
出典データセット
uspto-grants-2016_07
特許番号
US09399646B2

反応ノート

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