Aluminium lithium hydride → HCID 178519383, compound

HRID 1615194Notes

Reaction equation

HRID 1615194 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH:7]1[C:11]2[CH:12]=[CH:13][C:14]([C:16](OC)=[O:17])=[CH:15][C:10]=2[N:9]=[N:8]1>C1COCC1>[NH:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH2:16][OH:17])=[CH:15][C:10]=2[N:9]=[N:8]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 178497399HCID 178497399, compound

Product 1

HCID 178519383HCID 178519383, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere a dry round-bottom flask was charged with LiAlH4 (0.316 g, 7.90 mmol) and THF (15 mL). Methyl 1H-benzo[d][1,2,3]triazole-5-carboxylate (1.0 g, 5.64 mmol) was then added portion-wise over 10 min at room temperature and reaction allowed to stir for 4 hours at which time the reaction was quenched with EtOAc (5 mL), and the mixture poured into ice-water. The mixture was acidified to pH=3 with 10% H2SO4 and extracted 4× with EtOAc. The combined organics were washed with brine, dried (MgSO4) and the solvent removed. The resulting brown solid was boiled in Et2O and the solids filtered and dried to give the title compound as a light brown solid (678 mg, 81%). 1H NMR (400 MHz, CD3OD) δ 7.85 (m, 2H), 7.47 (d, J=8.4 Hz, 1H), 4.79 (s, 2H); MS ESI 150.0 [M+H]+, calcd for [C7H7N3O+H]+150.16.

Workup

  1. customreaction
  2. customwas quenched with EtOAc (5 mL)
  3. additionthe mixture poured into ice-water
  4. extractionextracted 4× with EtOAc
  5. washThe combined organics were washed with brine
  6. dry with materialdried (MgSO4)
  7. customthe solvent removed
  8. filtrationthe solids filtered
  9. customdried

Sources & evidence

ORD record
ord-3153a3e4134f4b749d0067c0c4062362
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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