Ammonium Chloride → (1-benzyl-1H-pyrazol-4-yl)methanol

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Reaction Steps

The ethyl 1-benzylpyrazole-4-carboxylate (5 g, 21.7 mmol) prepared in Example 9 was dissolved in THF (40 ml) and cooled to 0 degrees under inert atmosphere. Lithium Aluminum Hydride (1M in THF, 21.7 ml) was added dropwise. After complete addition, the solution was allowed to warm to room temperature and stirred for 2 hours. Saturated ammonium chloride solution was added slowly until gas evolution ceased. All solvent was removed in vacuo. To the residue was added 100 ml water and 250 ml ethyl acetate and placed in a separatory funnel. The organic layer was washed with water and concentrated to yield [1-benzylpyrazol-4-yl]methan-1-ol (3.8 g, HNMR)

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