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Sodium hydride → 3-[({[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]methyl}oxy)methyl]benzonitrile

HRID 606467
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HRID 606467 반응식
[C:1]1([C:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:8]2[CH:12]=[N:11][C:10]([CH2:13][OH:14])=[N:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:28][C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[C:32]#[N:33].[H-].[Na+]>C1COCC1>[C:21]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:8]2[CH:12]=[N:11][C:10]([CH2:13][O:14][CH2:28][C:29]3[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=3)[C:32]#[N:33])=[N:9]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1
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참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 97249Benzonitrile, 3-(bromomethyl)-HCID 13471694(1-trityl-1H-1,2,4-triazol-3-yl)methanol

생성물 1

HCID 667690183-[({[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]methyl}oxy)methyl]benzonitrile수율 87%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
70 °C

실험 절차

A suspension of [1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]methanol obtained in Reference Example 36 (3.00 g, 8.79 mmol), 3-(bromomethyl)benzonitrile (1.89 g, 9.67 mmol) and 60% sodium hydride (oil dispersion, 0.316 g, 13.2 mmol) in THF (100 mL) was stirred at 70° C. for 15 hr. The reaction mixture was cooled to room temperature, and extracted with water and ethyl acetate. The organic layer was washed with saturated brine, dried over sodium sulfate, and concentrated. The residue was purified by silica gel column chromatography (10-30% ethyl acetate/hexane) to give the title compound as a colorless oil (3.50 g, 87%).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with water and ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (10-30% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-0c3e3a2fbce9499bbea021a0575ccbc5
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07915267B2

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