Benzyl azide → 2-(1-benzyl-1H-1,2,3-triazol-4-yl)benzaldehyde

HRID 1040403

반응식

HRID 1040403 반응식
[C:1]([C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=[O:6])#[CH:2].[CH2:11]([N:18]=[N+:19]=[N-:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C)C=O.O>[CH2:11]([N:18]1[CH:2]=[C:1]([C:3]2[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=2[CH:5]=[O:6])[N:20]=[N:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH2:11]([N:18]1[C:1]([C:3]2[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=2[CH:5]=[O:6])=[CH:2][N:20]=[N:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

6

반응물 2

HCID 12152Benzyl azideHCID 6403682-Ethynylbenzaldehyde

생성물 2

HCID 866524202-(1-benzyl-1H-1,2,3-triazol-4-yl)benzaldehyde수율 65%HCID 866524212-(1-benzyl-1H-1,2,3-triazol-5-yl)benzaldehyde수율 30%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A solution of 2-ethynylbenzaldehyde (200 mg, 1.54 mmol) and benzyl azide (0.38 mL, 3.0 mmol) in 2.0 mL of N,N-dimethylformamide was stirred at 80° C. overnight. The reaction mixture was diluted with water, and the solution was extracted with a 5:1 solution (12 mL) of ethyl acetate and hexane. The extract was washed with water, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified with silica gel column chromatography (hexane/ethyl acetate=80/20 to 60/40) to obtain 2-(1-benzyl-1H-1,2,3-triazol-4-yl)benzaldehyde (259 mg, 65%) and 2-(1-benzyl-1H-1,2,3-triazol-5-yl)benzaldehyde (118 mg, 30%).

후처리

  1. extractionthe solution was extracted with a 5:1 solution (12 mL) of ethyl acetate and hexane
  2. washThe extract was washed with water, brine
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration
  5. concentrationthe filtrate was concentrated in vacuo
  6. customthe residue was purified with silica gel column chromatography (hexane/ethyl acetate=80/20 to 60/40)

출처 및 근거

ORD 기록
ord-5f6252eb299946e0bd73a3877ad94ae8
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08552220B2

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