Sodium hydride → (R)-6-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)picolinic acid

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Reaction Steps

Ethyl 6-hydroxypicolinate (500 mg, 2.7 mmol), (R)-(2,2-dimethyl-1,3-dioxolan-4-yl)methanol (1.11 mL, 3.0 eq) and NaH (60% dispersion in mineral oil, 385 mg, 3.3 eq) in THF was refluxed 18 hours. The reaction mixture was cooled to room temperature, acidified to pH=4, added to brine and extracted with ethyl acetate. The organic layer was dried, concentrated and recrystallized from pentane/ethylacetate to obtain (R)-6-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)picolinic acid (500 mg, 74% yield).

Provenance & Evidence