Lithium borohydride → HCID 18406865, compound

HRID 1016417Notes

Reaction equation

HRID 1016417 reaction equation
[N:1]1[C:2]([C:10](OCC)=[O:11])=[N:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.[BH4-].[Li+]>C1COCC1>[N:1]1[C:2]([CH2:10][OH:11])=[N:3][N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 5260536Ethyl [1,2,4]triazolo[1,5-a]pyridine-2-carboxylate

Product 1

HCID 18406865HCID 18406865, compoundYield 10.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To ethyl [1,2,4]triazolo[1,5-a]pyridine-2-carboxylate (prepared as described in J. Chem. Soc., Perkin Trans. 1, 1976, 2166) (0.67 g, 3.5 mmol) in THF (10 ml) was added lithium borohydride (78 mg, 3.6 mmol) and the mixture was stirred at room temperature under nitrogen overnight. The solvent was removed in vacuo and the residue was purified by flash chromatography on silica gel, eluting with 2.5 to 5% methanol in dichloromethane. The resultant solid was recrystallised from ethyl acetate, yielding [1,2,4]triazolo[1,5-a]pyridin-2-ylmethanol as a white solid (0.054 g). Data for the title compound: 1H NMR (400 MHz, CDCl3) δ 2.83 (1H, br s), 4.97 (2H, s), 7.03 (1H, t, J=6.9 Hz), 7.54 (1H, t, J=7.0 Hz), 7.72 (1H, d, J=9.0 Hz), 8.56 (1H, d, J=6.0 Hz); MS (ES+) m/e 150 [MH]+.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash chromatography on silica gel
  3. washeluting with 2.5 to 5% methanol in dichloromethane
  4. customThe resultant solid was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-25ff5744f87b4f3a9e1f18fcae72ddd5
Source dataset
uspto-grants-2002_11
Patent number
US06476030B1

Reaction notes

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