4-Nitrophenol → tert-Butyldimethyl(4-nitrophenoxy)silane

HRID 1419927

反応式

HRID 1419927 の反応式
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:11]([Si:15](Cl)([CH3:17])[CH3:16])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:11]([Si:15]([CH3:17])([CH3:16])[O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)([CH3:14])([CH3:13])[CH3:12]

参加物

6

反応物 3

HCID 9804-NitrophenolHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chloride

生成物 1

HCID 532659tert-Butyldimethyl(4-nitrophenoxy)silane収率 100%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

4-Nitrophenol (5.6 g, 40 mmol) was dissolved in CH2Cl2 (200 ml) and stirred at room temperature in the presence of tertbutyldimethyl-silyl chloride (7.8 g, 52 mmol), 4-dimethylaminopyridine (0.1 g, 0.8 mmol) and triethylamine (7.2 ml, 52 mmol). After 30 minutes at room temperature, the reaction mixture was washed with H2O (2×200 ml) and the resulting aqueous phases were extracted with CH2Cl2 (100 ml). The combined organic phases were dried over Na2SO4 and concentrated. The residue was chromatographed over silica gel (hexane-ether 9:1) to provide tert-Butyl-dimethyl-(4-nitro-phenoxy)-silane (10 g, 100%) as a yellow solid, m.p. 36°-38° C. and MS: m/e=253 (M+).

後処理

  1. washthe reaction mixture was washed with H2O (2×200 ml)
  2. extractionthe resulting aqueous phases were extracted with CH2Cl2 (100 ml)
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was chromatographed over silica gel (hexane-ether 9:1)

出典と根拠

ORDレコード
ord-f731cdad91b249178cadff74b1ee40cb
出典データセット
uspto-grants-1999_03
特許番号
US05889026

関連ノート

読み込み中…