Diethyl Ether → HCID 15204724, compound

Temperature

-20 °C

To a mixture of 3.59 g (0.019 mol) of o-bromobenzyl alcohol in 100 ml of ether cooled to -20° C. was added in portions 4.1 ml (0.0412 mol) of n-butyllithium (10M) in hexane over a 6 min period, and the reaction mixture was stirred 20 min. The above reaction mixture was cooled to -20° C., 3 g (0.021 mol) of 3-methoxy-pyridine-2-carboxaldehyde in 5 ml of THF was added in one portion to the mixture, and the resulting reaction mixture was allowed to warm to room temperature and stirred for 20 min. Ammonium chloride solution (30 ml) was added to the mixture and the mixture was extracted with ethyl acetate (3×50 ml). The organic layer was washed with brine, dried over sodium sulfate, and concentrated. The diol was triturated with 100 ml of ether, filtered, and purified by chromatography on silica gel eluting with 4% methanol/hexane. The solvent was concentrated in vacuo to afford 0.68 g (14.5%) of 2-[1-hydroxy-(2'-hydroxymethyl)benzyl]-3-methoxypyridine (Formula XIII: R1 =3--OCH3 ; R2 =R7 =H), as a white solid, m.p. 138°-140° C.

1. customThe above reaction mixture
2. temperaturewas cooled to -20° C.
3. customthe resulting reaction mixture
4. temperatureto warm to room temperature
5. stirringstirred for 20 min
6. extractionthe mixture was extracted with ethyl acetate (3×50 ml)
7. washThe organic layer was washed with brine
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated
10. customThe diol was triturated with 100 ml of ether
11. filtrationfiltered
12. custompurified by chromatography on silica gel eluting with 4% methanol/hexane
13. concentrationThe solvent was concentrated in vacuo

ORD record

ord-254c691901da4e74b9bc84e703c9b310

Source dataset

uspto-grants-1995_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05380729