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Hydrochloric Acid → 3-[5-Hydroxy-2-(4-hydroxyphenyl)-benzofuran-7-yl]-acrylamide

HRID 1836000
ノート
印刷プレビュー

反応式

HRID 1836000 の反応式
Br[C:2]1[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)=[CH:7][C:6]=2[CH:5]=[C:4]([OH:18])[CH:3]=1.[C:19]([NH2:23])(=[O:22])[CH:20]=[CH2:21].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.Cl>C(N(CC)CC)C.C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[OH:18][C:4]1[CH:3]=[C:2]([CH:21]=[CH:20][C:19]([NH2:23])=[O:22])[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)=[CH:7][C:6]=2[CH:5]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 6579AcrylamideHCID 80271Tri-o-tolylphosphineHCID 102863527-Bromo-2-(4-hydroxy-phenyl)-benzofuran-5-ol

生成物 1

HCID 688451963-[5-Hydroxy-2-(4-hydroxyphenyl)-benzofuran-7-yl]-acrylamide収率 51.8%

試薬・触媒・溶媒 3

HCID 167845
palladium(II) acetate
触媒
HCID 6342Acetonitrile溶媒
HCID 8471Triethylamine溶媒

実験手順

To a solution of 7-bromo-2-(4-hydroxy-phenyl)-benzofuran-5-ol 58 (0.3 g, 0.98 mmol) in triethylamine (5 mL) and acetonitrile (5 mL) was added acrylamide (0.077 g, 1.08 mmol) and tri-(o-tolyl) phosphine (0.060 g, 0.2 mmol). This mixture was purged with nitrogen for 10 minutes. Then palladium (II) acetate (0.022 g, 0.098 mmol) was added and the reaction was heated at reflux for 3.5 hours. To the cooled reaction was added 2N HCl and the product was extracted into ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and the solvent removed in vacuo. The residue was purified via flash chromatography on silica gel, eluting with 10% methanol in dichloromethane to give 0.15 g of 3-[5-hydroxy-2-(4-hydroxyphenyl)-benzofuran-7-yl]-acrylamide 61: Mp=275° C. (dec); 1H NMR (DMSO-d6) δ 9.89 (s, 1 H), 9.35 (s, 1 H), 7.86 (br s, 1 H), 7.83 (d, 2 H, J=8.6 Hz), 7.53 (d, 1 H, J=15.9 Hz), 7.23 (br s, 1 H), 7.11 (s, 1 H), 7.04 (d, 1 H, J=15.9 Hz), 6.94 (d, 1 H, J=2.4 Hz), 6.90 (d, 2 H, 8.7 Hz), 6.83 (d, 1 H, J=2.3 Hz); MS 296 (M+H)+

後処理

  1. customThis mixture was purged with nitrogen for 10 minutes
  2. temperaturethe reaction was heated
  3. temperatureat reflux for 3.5 hours
  4. customTo the cooled reaction
  5. extractionthe product was extracted into ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over MgSO4
  8. customthe solvent removed in vacuo
  9. customThe residue was purified via flash chromatography on silica gel
  10. washeluting with 10% methanol in dichloromethane

出典と根拠

ORDレコード
ord-54111cafc066416ea9596c8ad5068453
出典データセット
uspto-grants-2004_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06774248B2

反応ノート

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