Methyl iodide → 2-Ethyl-5-methoxypyridine

5-Methoxy-2-methyl-pyridine (9.5 g, 77 mmol) was added to a cooled −78° C. solution of LDA prepared from n-BuLi (37 mL, 93 mmol, 2.5 M in hexanes) and diisopropylamine (13 mL, 93 mmol) dissolved in THF (100 mL). The deep red reaction mixture was stirred for 30 mins and then treated with methyl iodide (5.4 mL, 85 mmol). After 2 hours the mixture was quenched with conc NH4OH (15 mL). The mixture was poured into H2O and extracted with EtOAc. The organic extracts were washed with brine, drived over Na2SO4 and concentrated to a red oil. Purification by flash column chromatography (0% to 40% EtOAc in hexanes) gave the product as a clear oil (2.5 g, 24%) and unreacted starting material (3.8 g, 40%). 1H NMR (400 MHz, CDCl3): δ 1.28 (t, J=7.3 Hz, 3 H), 2.76 (q, J=7.3 Hz, 2 H), 3.84 (s, 3 H), 7.08 (d, J=8.3 Hz, 1 H), 7.14 (d, J=8.3 Hz, 1 H), 8.23 (s, 1 H).

1. customThe deep red reaction mixture
2. customAfter 2 hours the mixture was quenched with conc NH4OH (15 mL)
3. additionThe mixture was poured into H2O
4. extractionextracted with EtOAc
5. washThe organic extracts were washed with brine
6. concentrationconcentrated to a red oil
7. customPurification by flash column chromatography (0% to 40% EtOAc in hexanes)

ORD record

ord-32c09bd771cc4081894496cd4ee29154

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08268835B2