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Water → {5-({[4-(Methyloxy)phenyl]methyl}oxy)-4-[(trimethylsilyl)ethynyl]-2-pyridinyl}methyl acetate

HRID 1038604
ノート
印刷プレビュー

反応式

HRID 1038604 の反応式
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][O:8][C:9]2[C:10](OS(C(F)(F)F)(=O)=O)=[CH:11][C:12]([CH2:15][O:16][C:17](=[O:19])[CH3:18])=[N:13][CH:14]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:37][Si:38]([C:41]#[CH:42])([CH3:40])[CH3:39].O>C(#N)C.[Cu](I)I>[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]([CH2:7][O:8][C:9]2[C:10]([C:42]#[C:41][Si:38]([CH3:40])([CH3:39])[CH3:37])=[CH:11][C:12]([CH2:15][O:16][C:17](=[O:19])[CH3:18])=[N:13][CH:14]=2)=[CH:5][CH:4]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 57423118(5-((4-Methoxybenzyl)oxy)-4-(((trifluoromethyl)sulfonyl)oxy)pyridin-2-yl)methyl acetate

生成物 1

HCID 57423117{5-({[4-(Methyloxy)phenyl]methyl}oxy)-4-[(trimethylsilyl)ethynyl]-2-pyridinyl}methyl acetate収率 504.6%

試薬・触媒・溶媒 2

HCID 83717
Copper iodide
触媒
HCID 6342Acetonitrile溶媒

反応条件

温度
45 °C

実験手順

(5-[(4-Methoxybenzyl)oxy]-4-{[(trifluoromethyl)sulfonyl]oxy}pyridin-2-yl)methylacetate (1.2 g, 2.78 mmol) was dissolved in acetonitrile (9.3 mL), added copper iodide (53 mg, 278 μmol), ditriphenylphosphine palladium (II) dichloride (98 mg, 139 μmol), triethylamine (8.0 mL) and trimethylsilyl acetylene (819 mg, 8.34 mmol) under an argon atmosphere, and under ice-cold conditions, and the mixture was stirred at 45° C. overnight. This operation was conducted for 4 lots, and the following treatments were conducted as a whole. The reaction solution was added water, and filtered through a pad of celite. The obtained filtrate was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. A crude product of the title compound (5.38 g) was obtained as a yellow oil.

後処理

  1. filtrationfiltered through a pad of celite
  2. extractionThe obtained filtrate was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-e1a69b817c5f419fb5c1b9d1e1a9dde6
出典データセット
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08551985B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート