Methanol → Methyl 6-(hydroxymethyl)picolinate

Into a 100-mL round-bottom flask, was placed a solution of 2,6-dimethylpyridine-2,6-dicarboxylate (950 mg, 4.87 mmol, 1.00 equiv) in a solvent mixture of methanol (33.2 mL) and dichloromethane (14.2 mL). NaBH4 (185 mg, 5.02 mmol, 1.00 equiv) was added to the reaction mixture in several batches at 0° C. The resulting solution was stirred overnight at room temperature, and then it was quenched by the addition of 50 mL of NH4Cl (aq.). The resulting solution was extracted with 2×50 mL of dichloromethane and the combined organic layers were dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:1-2:1) as eluent to yield 750 mg (92%) of methyl 6-(hydroxymethyl)pyridine-2-carboxylate as a white solid.

1. customInto a 100-mL round-bottom flask, was placed
2. customit was quenched by the addition of 50 mL of NH4Cl (aq.)
3. extractionThe resulting solution was extracted with 2×50 mL of dichloromethane
4. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
5. concentrationconcentrated under vacuum

ORD record

ord-a38389f00f73419d948845fdffbdefa0

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09012450B2