Methyl iodide → 6-Ethylpicolinaldehyde

To a solution of N,N,N-trimethylethylenediamine (4.29 mL, 33 mmol) in THF (20 mL) at -25° C. was added n-BuLi (13.2 mL, 2.5M in hexanes, 33 mmol). This solution was stirred 15 minutes, then transferred into a -78° C. solution of 6-methyl-2-pyridine-carboxaldehyde (3.63 g, 30 mmol) in THF (80 mL). After stirring 30 minutes at -78° C., a THF (50 mL) solution of lithium diisopropylamide (33 mmol) was added and the now dark red mixture was stirred 1 hour at -78° C. Methyl iodide (5.68 g, 40 mmol) in THF (10 mL) was added and reaction mixture was allowed to warm to r.t. for 4 hours. Water and 25% aq. NH4OAc were added, the crude product was extracted with EtOAc (2×) and solvents were evaporated. Purification by flash chromatography (from 5% to 10% EtOAc in hexanes) gave 660 mg of the title compound.

1. customtransferred into a -78° C.
2. stirringAfter stirring 30 minutes at -78° C.
3. stirringthe now dark red mixture was stirred 1 hour at -78° C
4. customreaction mixture
5. extractionthe crude product was extracted with EtOAc (2×) and solvents
6. customwere evaporated
7. customPurification by flash chromatography (from 5% to 10% EtOAc in hexanes)

ORD record

ord-76c1fa65a7d240268a11ca50006883b0

Source dataset

uspto-grants-1996_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05506227