2-Bromoethanol → 2-(5-(Methoxymethoxy)-2-methylpyridin-4-yloxy)ethanol

Temperature

90 °C

To a solution of 5-(methoxymethoxy)-2-methylpyridin-4(1H)-on (1.28 g, 7.56 mmol) in N,N′-dimethylformamide (19 mL), potassium carbonate (2.10 g, 15.1 mmol) and 2-bromoethanol (804 μL, 11.3 mmol) were added sequentially, and the mixture was stirred at 90° C. overnight. After the reaction has terminated, the reaction solution was concentrated in vacuo. The obtained residue was dissolved in chloroform/methanol, the solids were filtered, and the filtrate was concentrated in vacuo. The obtained residue was purified by column chromatography (hexane/acetone) and 2-(5-(methoxymethoxy)-2-methylpyridin-4-yloxy)ethanol (900 mg, yield 56%) was obtained as an orange oil.

1. customAfter the reaction has terminated
2. concentrationthe reaction solution was concentrated in vacuo
3. dissolutionThe obtained residue was dissolved in chloroform/methanol
4. filtrationthe solids were filtered
5. concentrationthe filtrate was concentrated in vacuo
6. customThe obtained residue was purified by column chromatography (hexane/acetone)

ORD record

ord-d60ab941f267448d81042c0e2f522549

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08551985B2