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

HRID 494981노트

반응식

HRID 494981 반응식
[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]

참가 물질

6

반응물 3

HCID 795Imidazole2회HCID 28928tert-Butyldimethylsilyl chloride2회HCID 576827814-Allyl-5-methoxy-2-nitrobenzyl alcohol

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-c4aa03e07fbf41439164c39926bfc7bc
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538123B2

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