Water → (2,6-Dichloropyridin-3-yl)methanol

Participants

Reaction Conditions

Reaction Steps

Dissolve 2,6-dichloronicotinic acid (1000 mg, 5.21 mmol) in anhydrous tetrahydrofuran (5 mL). Cool to 0° C. Add borane-tetrahydrofuran complex (7.82 mL, 7.82 mmol, 1.0 M in tetrahydrofuran) slowly. Stir the mixture at room temperature overnight. Add water (1 mL) and potassium carbonate, stir for 2 hours, filter and concentrate to give a residue. Chromatograph the residue on silica gel eluting with 10:90 to 20:80 ethyl acetate:hexanes to give (2,6-dichloropyridin-3-yl)-methanol (876 mg, 94%). 1H NMR (400 MHz, MeOH-d4) δ 7.96 (d, 1H, J=8.0 Hz), 7.45 (d, 1H, J=8.0 Hz), 4.64 (s, 2H).

Provenance & Evidence