Sodium borohydride → (3,4-Difluoro-2-pyridinyl)methanol
Reaction equation
[F:1][C:2]1[C:3]([CH:9]=[O:10])=[N:4][CH:5]=[CH:6][C:7]=1[F:8].[BH4-].[Na+]>C(O)C>[F:1][C:2]1[C:3]([CH2:9][OH:10])=[N:4][CH:5]=[CH:6][C:7]=1[F:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Intermediate 5 (142 mg, 0.992 mmol) was dissolved in ethanol (5 mL) under N2(g) atmosphere. Sodium borohydride (ALDRICH, 113 mg, 2.98 mmol) was added and mixture of reaction was stirred for 1 hour. Crude of reaction was partitioned between DCM (15 mL) and distilled water (15 mL). Aqueous layer was extracted with DCM (2×15 mL). Organic layers were dried over MgSO4(anh), filtered and concentrated to yield title compound (3,4-difluoro-2-pyridinyl)methanol (140 mg, 0.965 mmol, 97% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm: 8.37-8.40 (m, 1H), 7.50-7.55 (m, 1H), 5.45 (t, 1H), 4.61-4.63 (m, 2H). [ES+MS] m/z 146 (MH+).