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1H-1,2,4-Triazole → 3,3-Dimethyl-2-{2-[4-(1,3-dioxolan-2-yl)-phenyl]-ethenyl}-1-(1,2,4-triazol-1-yl)-2-butanol

HRID 464692
ノート
印刷プレビュー

反応式

HRID 464692 の反応式
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14]2([C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:16][O:15]2)=[CH:8][CH:7]=1.N1C=[C-]N=N1.[Na+].[NH:27]1[CH:31]=[N:30][CH:29]=[N:28]1.[H-].[Na+]>CN(C)C=O>[CH3:18][C:17]([CH3:20])([CH3:19])[C:14]([CH:13]=[CH:12][C:9]1[CH:10]=[CH:11][C:6]([CH:2]2[O:3][CH2:4][CH2:5][O:1]2)=[CH:7][CH:8]=1)([OH:15])[CH2:16][N:27]1[CH:31]=[N:30][CH:29]=[N:28]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 201978292-{2-[4-(1,3-Dioxolan-2-yl)-phenyl]-ethenyl}-2-tert.-butyl-oxiraneHCID 129663835Sodium triazolide

生成物 1

HCID 544901003,3-Dimethyl-2-{2-[4-(1,3-dioxolan-2-yl)-phenyl]-ethenyl}-1-(1,2,4-triazol-1-yl)-2-butanol収率 24.3%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒
2 回

反応条件

温度
80 °C

実験手順

25.6 g (0.093 mol) of 2-{2-[4-(1,3-dioxolan-2-yl)-phenyl]-ethenyl}-2-tert.-butyl-oxirane in 47 ml of absolute dimethylformamide are added dropwise, at room temperature, to a solution of sodium triazolide, prepared by slowly introducing 12.9 g (0.187 mol) of 1,2,4-triazole into a suspension of 5.6 g (0.187 mol) of sodium hydride (80% strength in paraffin oil) in 187 ml of absolute dimethylformamide. The reaction mixture is stirred at 80° C. for 4 hours and left to stand overnight at room temperature. Thereafter, the reaction mixture is poured onto ice water and extracted several times with ethyl acetate. The combined ethyl acetate phases are washed twice with water and once with saturated sodium chloride solution, dried over sodium sulphate and concentrated. The residue is chromatographed over a silica gel column (methylene chloride/ethyl acetate=2:1) and the product is recrystallized from n-hexane/ethyl acetate. 7.75 g (24% of theory) of 3,3-dimethyl-2-{2-[4-(1,3-dioxolan-2-yl)-phenyl]-ethenyl}-1-(1,2,4-triazol-1-yl)-2-butanol of melting point 109.5°-110° C. are obtained.

後処理

  1. customprepared
  2. waitleft
  3. waitto stand overnight at room temperature
  4. additionThereafter, the reaction mixture is poured onto ice water
  5. extractionextracted several times with ethyl acetate
  6. washThe combined ethyl acetate phases are washed twice with water and once with saturated sodium chloride solution
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated
  9. customThe residue is chromatographed over a silica gel column (methylene chloride/ethyl acetate=2:1)
  10. customthe product is recrystallized from n-hexane/ethyl acetate

出典と根拠

ORDレコード
ord-59fd0999f85a426593fc160475a84e86
出典データセット
uspto-grants-1985_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04548945

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート