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Imidazole → Benzoic acid, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, methyl ester

HRID 1699739
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HRID 1699739 반응식
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[CH:5]=1.N1C=CN=C1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].[Cl-].[NH4+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH:5]=1
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참가 물질

6

반응물 4

HCID 795ImidazoleHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 88068Methyl 3-Hydroxybenzoate

생성물 1

HCID 11715937Benzoic acid, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, methyl ester수율 98%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
0 °C

실험 절차

1.53 g of 3-hydroxybenzoic acid methyl ester and 1.69 g of imidazole were placed in a 50 ml flask, and a gas in the reaction system was replaced with nitrogen. 5 ml of DMF was added into the flask and stirred at 0° C. The obtained solution was mixed with 1.57 g of t-butyldimethylsilyl chloride, heated up to room temperature, simultaneously stirred overnight, and then mixed with a saturated aqueous solution of ammonium chloride to stop the reaction. The reaction solution was extracted with diethyl ether, and the obtained organic layer was sequentially washed with water, a saturated aqueous solution of potassium hydrogen sulfate and a saturated aqueous solution of sodium chloride and then dried over magnesium sulfate. The solvent was distilled away under reduced pressure to obtain 1.69 g of the title compound. Yield: 98%.

후처리

  1. temperatureheated up to room temperature, simultaneously stirred overnight
  2. customthe reaction
  3. extractionThe reaction solution was extracted with diethyl ether
  4. washthe obtained organic layer was sequentially washed with water
  5. dry with materiala saturated aqueous solution of potassium hydrogen sulfate and a saturated aqueous solution of sodium chloride and then dried over magnesium sulfate
  6. distillationThe solvent was distilled away under reduced pressure

출처 및 근거

ORD 기록
ord-2e9693b4154849e39a7da7d17050cc96
출처 데이터셋
uspto-grants-2002_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06348478B1

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