Methyl 6-methylnicotinate → (6-Methylpyridin-3-yl)methanol

To a suspension of lithium aluminium hydride (7.24 g, 191 mmol) in Et2O (400 ml) at −78° C. was added via cannula over a period of one hour a solution of methyl 6-methylnicotinate (19.62 g, 130 mmol) in Et2O (200 mL). Once addition was completed, the mixture was stirred for a further 3 h. Excess lithium aluminium hydride was quenched by dropwise addition of EtOAc (40 ml). The mixture was then warmed using a water-ice bath, and further quenched with sat NH4Cl (500 mL). The ethereal layer was decanted, and EtOAc was added (500 mL). The mixture was stirred vigorously, and the organic layer was again decanted. The extraction procedure was repeated twice (500 mL EtOAc). The combined organic extracts were dried (MgSO4) and concentrated to yield the desired product (13.6 g, 85%). 1H NMR (300 MHz, CDCl3) δ: 8.39 (1H, s), 7.62 (1H, dd, J=2.1, 8.1 Hz), 7.14 (1H, d, J=7.8 Hz), 4.68 (2H, s), 2.54 (3H, s).

1. additionOnce addition
2. customExcess lithium aluminium hydride was quenched by dropwise addition of EtOAc (40 ml)
3. temperatureThe mixture was then warmed
4. customfurther quenched with sat NH4Cl (500 mL)
5. customThe ethereal layer was decanted
6. additionEtOAc was added (500 mL)
7. stirringThe mixture was stirred vigorously
8. customthe organic layer was again decanted
9. extractionThe extraction procedure
10. dry with materialThe combined organic extracts were dried (MgSO4)
11. concentrationconcentrated

ORD record

ord-7488dc98741b4c9e9a6a859244539bc0

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09273003B2