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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
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HRID 464692 반응식
[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
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참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매
2회

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-59fd0999f85a426593fc160475a84e86
출처 데이터셋
uspto-grants-1985_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04548945

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