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

HRID 509300Notes

Reaction equation

HRID 509300 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-b0fc0ec635994b9482bc2e9cf83c03ac
Source dataset
uspto-grants-2015_08
Patent number
US09096559B2

Reaction notes

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