Lithium borohydride → [1,2,4]Triazolo[1,5-a]pyridin-2-ylmethanol
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]=12Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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]+.