Water → ethyl 2-[1-benzyl-5-(3,4-dihydro-2H-1-benzopyran-6-yl)-3-(trifluoromethyl)-1H-pyrazol-4-yl]-2-hydroxyacetate

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Reaction Steps

Under a nitrogen atmosphere, sodium borohydride (6.44 mg, 0.17 mmol) was added portionwise to a solution of ethyl 2-[1-benzyl-5-(3,4-dihydro-2H-1-benzopyran-6-yl)-3-(trifluoromethyl)-1H-pyrazol-4-yl]-2-oxoacetate (49e) (78 mg, 0.17 mmol) in anhydrous methanol (2 mL). After 2 hours stirring, water was added (3 mL). The methanol was removed under reduced pressure, and the aqueous layer was extracted with ethyl acetate (2×5 mL). The organic layer was successively washed with water (3 mL) and brine (3 mL), before being dried over sodium sulfate and concentrated in vacuo to provide the desired alcohol (49f) (70 mg, 0.17 mmol, 89%) which was used without further purification.

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