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Trimethylsilane → {5-Hydroxy-4-[(trimethylsilyl)ethynyl]-2-pyridinyl}methyl acetate

HRID 1038605
ノート
印刷プレビュー

反応式

HRID 1038605 の反応式
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([C:12]#[C:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[C:9]([O:18]CC2C=CC(OC)=CC=2)=[CH:8][N:7]=1)(=[O:3])[CH3:2].C[SiH](C)C.FC(F)(F)C([O-])=O.C(=O)([O-])O.[Na+]>ClCCl>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([C:12]#[C:13][Si:14]([CH3:15])([CH3:17])[CH3:16])[C:9]([OH:18])=[CH:8][N:7]=1)(=[O:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 70435TrimethylsilaneHCID 84468TrifluoroacetateHCID 516892Sodium BicarbonateHCID 57423117{5-({[4-(Methyloxy)phenyl]methyl}oxy)-4-[(trimethylsilyl)ethynyl]-2-pyridinyl}methyl acetate

生成物 1

HCID 57423119{5-Hydroxy-4-[(trimethylsilyl)ethynyl]-2-pyridinyl}methyl acetate収率 53%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

(5-((4-Methoxybenzyl)oxy)-4-((trimethylsilyl)ethynyl)pyridin-2-yl)methyl acetate (5.38 g, 11.1 mmol) which is a crude product obtained in a-5) was dissolved in dichloromethane (55 mL), added trimethylsilane (1.9 mL, 35.1 mmol) and trifluoroacetate (5.5 mL) at room temperature, and the mixture was stirred overnight. The reaction solution was added a saturated aqueous solution of sodium hydrogen carbonate under ice-cold conditions (pH=8 was confirmed). The reaction solution was 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. The obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate), and the title compound (1.54 g (yield 53%)) was obtained as a yellow oil.

後処理

  1. customobtained in a-5)
  2. filtrationThe reaction solution was filtered through a pad of celite
  3. extractionThe obtained filtrate was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe obtained residue was purified by silica-gel column chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-e0fc05b143dc4d9b9ee0970151055544
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

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