Sodium borohydride → (4-Iodo-2-methoxy-pyridin-3-yl)methanol

Solid NaBH4 (28 mg, 0.74 mmol) was added in one portion to a solution of 3-formyl-4-iodo-2-methoxypyridine (prepared according to the method of Fang et al., J. Org. Chem., 1994, 59, 6142) (98 mg, 0.37 mmol) in methanol (4 mL) at −5° C. Vigorous bubbling was observed and the yellow reaction solution turned colorless. The reaction was immediately quenched by the addition of water (2 mL) and the methanol was removed under reduced pressure. The resulting residue was diluted with ethyl acetate (20 mL) and water (20 mL). The aqueous layer was separated and extracted with ethyl acetate (3×10 mL). The organic fractions were combined, dried (MgSO4), filtered and concentrated to give 3-(hydroxymethyl)-4-iodo-2-methoxypyridine as a colorless, crystalline solid. This material was used in the next reaction without further purification. R/0.4 (30% ethyl acetate/petrol elution). MS (APCI, m/z 266 (M++1, 100%). 1H NMR (200 MHz, CDCl3): δ3.98 (s, 3H), 4.80 (s, 2H), 7.34 (d, J=4.0 Hz, 1H), 7.70 (d, J=4.0 Hz, 1H).

1. customprepared
2. customat −5° C
3. customVigorous bubbling
4. customThe reaction was immediately quenched by the addition of water (2 mL)
5. customthe methanol was removed under reduced pressure
6. additionThe resulting residue was diluted with ethyl acetate (20 mL) and water (20 mL)
7. customThe aqueous layer was separated
8. extractionextracted with ethyl acetate (3×10 mL)
9. dry with materialdried (MgSO4)
10. filtrationfiltered
11. concentrationconcentrated

ORD 기록

ord-c1101b4a476147658526f0d5e5caccbb

출처 데이터셋

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06355683B1