4-Iodophenol → 1-Iodo-4-[(2-methylbut-3-yn-2-yl)oxy]benzene

HRID 847171ノート

反応式

HRID 847171 の反応式
Cl[C:2]([CH3:6])([CH3:5])[C:3]#[CH:4].[I:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>[CH3:5][C:2]([O:14][C:11]1[CH:12]=[CH:13][C:8]([I:7])=[CH:9][CH:10]=1)([CH3:6])[C:3]#[CH:4]

参加物

7

反応物 3

HCID 108944-IodophenolHCID 14798Sodium HydroxideHCID 706791-Butyne, 3-chloro-3-methyl-

生成物 1

HCID 149335571-Iodo-4-[(2-methylbut-3-yn-2-yl)oxy]benzene収率 30%

試薬・触媒・溶媒 3

HCID 94433Tetrabutylammonium hydrogen sulfate触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

A solution of 3-chloro-3-methyl-1-butyne (10.0 g, 97.9 mmol), 4-iodophenol (15.0 g, 68.4 mmol), sodium hydroxide (3.90 g, 97.5 mmol) and tetrabutylammonium hydrogen sulfate (9.33 g, 27.5 mmol) in methylene chloride (50 mL) and water (50 mL) was stirred for 19 days at room temperature. After separating the two layers, the organic layer was washed with 1 N sodium hydroxide followed by water, dried over magnesium sulfate and concentrated in vacuo. The residue was dissolved in ethyl acetate and washed successively with 1 N hydrochloric acid, 1 N sodium hydroxide, water, brine and dried over anhydrous magnesium sulfate. After removing drying agent, the solvent was removed in vacuo. The crude product was purified by flash chromatography on silica gel eluting with toluene/hexane (1:10) to give the title compound as an oil (5.78 g, 20.2 mmol) in 30% yield: 1H NMR (CDCl3) δ 7.56 (d, J=8.7 Hz, 2H), 6.98 (d, J=8.8 Hz, 2H), 2.56 (s, 1H), 1.63 (s, 6H); 13C NMR (CDCl3) δ 155.4, 137.8, 123.5, 86.0, 85.6, 74.3, 72 6, 29.5.

後処理

  1. customAfter separating the two layers
  2. washthe organic layer was washed with 1 N sodium hydroxide
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed successively with 1 N hydrochloric acid, 1 N sodium hydroxide, water, brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customAfter removing
  9. customdrying agent
  10. customthe solvent was removed in vacuo
  11. customThe crude product was purified by flash chromatography on silica gel eluting with toluene/hexane (1:10)

出典と根拠

ORDレコード
ord-8b4f1d5ea1fe4a618110b36a9ef2daa6
出典データセット
uspto-grants-1992_08
特許番号
US05140031

反応ノート

読み込み中…