Water → 1-[2-(4-nitro-benzyloxy)-ethyl]-1H-[1,2,3]triazole

HRID 1271423

반응식

HRID 1271423 반응식
[N:1]1([CH2:6][CH2:7][OH:8])[CH:5]=[CH:4][N:3]=[N:2]1.[H-].[Na+].I[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1.O>C1COCC1.C(OCC)(=O)C>[N+:19]([C:16]1[CH:17]=[CH:18][C:13]([CH2:12][O:8][CH2:7][CH2:6][N:1]2[CH:5]=[CH:4][N:3]=[N:2]2)=[CH:14][CH:15]=1)([O-:21])=[O:20]

참가 물질

7

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 76598alpha-Iodo-p-nitrotolueneHCID 99892372-(1H-1,2,3-triazol-1-yl)ethan-1-ol

생성물 1

HCID 184535171-[2-(4-nitro-benzyloxy)-ethyl]-1H-[1,2,3]triazole수율 27.4%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2-[1,2,3]triazol-1-yl-ethanol (5.98 g, 52.84 mmol) in dry THF (150 ml) at −50° C. sodium hydride (1.27 g, 52.84 mmol) was added and the mixture stirred for 45 min. followed by the addition of 1-iodomethyl-4-nitro-benzene (13.9 g, 52.84 mmol). The mixture was refluxed for 2 h, water (100 ml) and ethyl acetate (150 ml) were added and the resulting precipitate removed by filtration. The filtrate was concentrated and the residue purified by flash column chromatography (ethyl acetate 100%) yielding 3.6 g (27%) 1-[2-(4-nitro-benzyloxy)-ethyl]-1H-[1,2,3]triazole.

후처리

  1. temperatureThe mixture was refluxed for 2 h
  2. customthe resulting precipitate removed by filtration
  3. concentrationThe filtrate was concentrated
  4. customthe residue purified by flash column chromatography (ethyl acetate 100%)

출처 및 근거

ORD 기록
ord-f64892ae18c344a4b8f049209f3376eb
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07205326B2

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