2,6-Dichloro-isonicotinoyl chloride → (2,6-Dichloropyridin-4-yl)methanol

Participants

Reaction Conditions

Reaction Steps

2,6-Dichloro-isonicotinoyl chloride (11-1, 2.31 g, 11.0 mmol) was dissolved in 20 mL of anhydrous THF in an oven dried flask under N2. The solution was cooled to 0° C. and LiBH4 (2 M solution in THF, 3.29 mL, 6.59 mmol) was added dropwise. After 1 hour the reaction was quenched by the addition of 1M HCl. After 10 minutes the mixture was diluted with saturated NaHCO3 (aq). The aqueous phase was extracted 3× with DCM. The combined organic phases were dried over Na2SO4, filtered and concentrated to afford 11-2 as a white solid. 1H NMR (CDCl3) δ 7.30 (s, 2H), 4.75 (d, 2H), 2.15 (t, 1H). MS [M+H]+=178.0.

Provenance & Evidence