Sodium borohydride → (4-Iodopyridin-2-yl)methanol

Participants

Reaction Steps

To a solution of methyl 4-iodopicolinate 5AN (2.83 g, 10.78 mmol) in MeOH (30 ml) was added NaBH4 (1.59 g, 43.12 mmol) portion wise at 0° C. Reaction mixture was allowed to warm up to r.t. After stirring for 3 days at r.t, it was quenched with, 14 ml of 1N NaOH. Reaction mixture was diluted with DCM (200 ml). The organic layer was washed with water (2×30 ml), dried over MgSO4, filtered and concentrated. The residue was purified on silica gel eluting with 3/1 EtOAc/Hexane to give the desired product (4-iodo-pyridin-2-yl)-methanol 6AN (2.27 g, 90%).

Provenance & Evidence