Oxyselenide → (4-Methyl-5-nitropyridin-2-yl)methanol

To a solution of the mixture of 2,4-dimethyl-5-nitropyridine (3.0 g, 20 mmol) in 30 ml of dioxane, was selenium oxide (2.8 g, 25 mmol) added at an ambient temperature. The reaction was refluxed for 10 hrs. The reaction was cooled to room temperature and concentrated under vacuum. The residue was poured into water and extracted with ethyl acetate. The organic layer was dried over MgSO4 and concentrated under vacuum. The crude mixture of the aldehyde was diluted in methanol (30 mL) and sodium borohydride (0.74 g, 20 mmol) was added portionwise at 0° C. After stirred for 1 hr, the reaction was quenched with water (20 mL) and concentrated under vacuum. The reaction was extracted with ethyl acetate and dried over MgSO4. The ethyl acetate was dried under vacuum and purified under SiO2 with 50% ethyl acetate in hexane to afford (4-methyl-5-nitropyridin-2-yl)methanol in 83% (2.7 g). 1HNMR (CDCl3, 400 MHz) δ 2.65 (s, 1H), 4.60 (d, J=8.1, 2H), 5.81 (t, J=8.1, 1H), 7.67 (s, 1H), 9.21 (s, 1H).

1. additionadded at an ambient temperature
2. temperatureThe reaction was refluxed for 10 hrs
3. concentrationconcentrated under vacuum
4. additionThe residue was poured into water
5. extractionextracted with ethyl acetate
6. dry with materialThe organic layer was dried over MgSO4
7. concentrationconcentrated under vacuum
8. additionThe crude mixture of the aldehyde
9. additionwas diluted in methanol (30 mL)
10. customthe reaction was quenched with water (20 mL)
11. concentrationconcentrated under vacuum
12. extractionThe reaction was extracted with ethyl acetate
13. dry with materialdried over MgSO4
14. dry with materialThe ethyl acetate was dried under vacuum
15. custompurified under SiO2 with 50% ethyl acetate in hexane

ORDレコード

ord-7d105d4ae45a4e0ebb1bdb08e95359af

出典データセット

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08362248B2