Imidazole → (4-Allyl-5-methoxy-2-nitrobenzyloxy)-t-butyldimethylsilane

HRID 494981ノート

反応式

HRID 494981 の反応式
[CH2:1]([C:4]1[C:11]([O:12][CH3:13])=[CH:10][C:7]([CH2:8][OH:9])=[C:6]([N+:14]([O-:16])=[O:15])[CH:5]=1)[CH:2]=[CH2:3].N1C=CN=C1.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([C:4]1[C:11]([O:12][CH3:13])=[CH:10][C:7]([CH2:8][O:9][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])=[C:6]([N+:14]([O-:16])=[O:15])[CH:5]=1)[CH:2]=[CH2:3]

参加物

6

反応物 3

HCID 795Imidazole2 回HCID 28928tert-Butyldimethylsilyl chloride2 回HCID 576827814-Allyl-5-methoxy-2-nitrobenzyl alcohol

生成物 1

HCID 57682929(4-Allyl-5-methoxy-2-nitrobenzyloxy)-t-butyldimethylsilane収率 95.3%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

229 mg of 4-allyl-5-methoxy-2-nitrobenzyl alcohol was dissolved in 5 ml of N,N-dimethylformamide. Thereafter, 0.17 g of imidazole and 0.23 g of t-butyldimethylsilyl chloride were added to the reaction solution while cooling on ice. The obtained mixture was stirred at room temperature for 2 hours. Thereafter, 34 mg of imidazole and 46 mg of t-butyldimethylsilyl chloride were further added to the reaction solution. The obtained mixture was stirred at room temperature overnight. The reaction solution was diluted with ethyl acetate and then washed with a saturated ammonium chloride aqueous solution and a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate), so as to obtain 330 mg of the subject compound.

後処理

  1. temperaturewhile cooling on ice
  2. stirringThe obtained mixture was stirred at room temperature overnight
  3. washwashed with a saturated ammonium chloride aqueous solution
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under a reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-c4aa03e07fbf41439164c39926bfc7bc
出典データセット
uspto-grants-2009_05
特許番号
US07538123B2

反応ノート

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