Aluminium lithium hydride → (1-((Trimethylsilyl)methyl)-1h-1,2,3-triazol-4-yl)methanol

HRID 509300

반응식

HRID 509300 반응식
[CH3:1][Si:2]([CH2:5][N:6]1[CH:10]=[C:9]([C:11](OCC)=[O:12])[N:8]=[N:7]1)([CH3:4])[CH3:3].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:4][Si:2]([CH2:5][N:6]1[CH:10]=[C:9]([CH2:11][OH:12])[N:8]=[N:7]1)([CH3:1])[CH3:3]

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 59627360ethyl 1-[(trimethylsilyl)methyl]-1H-1,2,3-triazole-4-carboxylate

생성물 1

HCID 59627317(1-((Trimethylsilyl)methyl)-1h-1,2,3-triazol-4-yl)methanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

A solution of ethyl 1-[(trimethylsilyl)methyl]-1H-1,2,3-triazole-4-carboxylate (1.00 g, 4.40 mmol) and THF (14.6 mL) was cooled to 0° C. and a solution of LAH (4.40 mL, 1M in THF) was added dropwise. The mixture was stirred for 1 h, and the cold bath was removed and stirred for an additional hour. The reaction was cooled to 0° C. and a solution of saturated sodium sulfate (4.4 mL) was added. The mixture was warmed to room temperature, stirred 30 min, and filtered. The filtrate was concentrated and the residue azeotroped with ethanol to afford a colorless oil purified via MPLC, 40M column, 1-8% MeOH in DCM afforded the title material as a clear, colorless oil. MS: cal'd 186 (MH+), exp 186 (MH+).

후처리

  1. customthe cold bath was removed
  2. stirringstirred for an additional hour
  3. additiona solution of saturated sodium sulfate (4.4 mL) was added
  4. temperatureThe mixture was warmed to room temperature
  5. stirringstirred 30 min
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customthe residue azeotroped with ethanol
  9. customto afford a colorless oil
  10. custompurified via MPLC, 40M column, 1-8% MeOH in DCM

출처 및 근거

ORD 기록
ord-b0fc0ec635994b9482bc2e9cf83c03ac
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096559B2

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