Methyl 2-methoxyisonicotinate → (2-Methoxypyridin-4-yl)methanol

Temperature

70 °C

To a 100-mL round-bottomed flask was added methyl 2-methoxyisonicotinate (2.04 mL, 14.12 mmol, Aldrich, St. Louis, Mo.) and borane methyl sulfide complex (4.02 mL, 42.4 mmol, Aldrich, St. Louis, Mo.) in THF (30 mL). The reaction mixture was stirred at 70° C. for 18 h, cooled to 0° C. and quenched by the addition of MeOH (5 mL), followed by 1N NaOH (20 mL). The reaction mixture was extracted with EtOAc (2×50 mL), the organic extract was washed with saturated NaCl (20 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as a light-yellow oil. The crude product was purified by silica gel chromatography, eluting with 60% EtOAc/hexanes to give (2-methoxy-4-pyridinyl)methanol (1.56 g) as colorless oil.

1. temperaturecooled to 0° C.
2. customquenched by the addition of MeOH (5 mL)
3. extractionThe reaction mixture was extracted with EtOAc (2×50 mL)
4. extractionthe organic extract
5. washwas washed with saturated NaCl (20 mL)
6. dry with materialdried over Na2SO4
7. filtrationThe solution was filtered
8. concentrationconcentrated in vacuo
9. customto give the crude material as a light-yellow oil
10. customThe crude product was purified by silica gel chromatography
11. washeluting with 60% EtOAc/hexanes

ORD record

ord-ab7888e66f6a44108e4969c89cf3d760

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08431563B2