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

HRID 1271423ノート

反応式

HRID 1271423 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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%)

出典と根拠

ORDレコード
ord-f64892ae18c344a4b8f049209f3376eb
出典データセット
uspto-grants-2007_04
特許番号
US07205326B2

反応ノート

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