Borane → (6-(2-Methoxyethoxy)pyridin-3-yl)methanol

Temperature

0 °C

6-(2-methoxyethoxy)nicotinic acid (3.94 g 20.0 mmol) was dissolved in anhydrous THF (80 ml) and cooled to 0° C., and stirred under argon while a solution of 1M borane in THF (80 ml) was added over a period of 1 hour. The mixture was allowed to warm to room temperature and left to stir for 4 hours to complete the reaction. The reaction was cooled to 0° C., and quenched by the careful addition of methanol (20 ml total) in small aliquots. The mixture was allowed to stir overnight to complete the quench, then concentrated to dryness in vacuo. The solids were partitioned between ethyl acetate (100 ml) and saturated Na2CO3 (50 ml), and separated, then the aqueous extracted again with ethyl acetate (100 ml). The combined organics were washed with brine (50 ml), then dried (MgSO4) and concentrated in vacuo to give the crude product as clear oil (2.86 g).

1. additionwas added over a period of 1 hour
2. temperatureto warm to room temperature
3. waitleft
4. customthe reaction
5. temperatureThe reaction was cooled to 0° C.
6. customquenched by the careful addition of methanol (20 ml total) in small aliquots
7. stirringto stir overnight
8. concentrationconcentrated to dryness in vacuo
9. customThe solids were partitioned between ethyl acetate (100 ml) and saturated Na2CO3 (50 ml)
10. customseparated
11. extractionthe aqueous extracted again with ethyl acetate (100 ml)
12. washThe combined organics were washed with brine (50 ml)
13. dry with materialdried (MgSO4)
14. concentrationconcentrated in vacuo

ORD record

ord-ad3ec85ac83c4923bfeac93dfda51ad1

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08710224B2