3-Pyridinemethanol → Ethyl 2-((pyridin-3-yl)methoxy)acetate

Temperature

27 °C

To a solution of NaH (330 mg, 13.7 mmol) in DMF (10 mL) was added pyridin-3-ylmethanol (500 mg, 4.6 mmol) and the solution was stirred at 27° C. for 20 minutes. Ethyl 2-bromoacetate (921.8 mg, 5.52 mmol) was then added and the reaction mixture stirred at 27° C. for further 16 h. Once the reaction was complete by TLC analysis, the mixture was quenched by addition of water (50 mL) and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine (30 mL), dried over Na2SO4 and concentrated to give the Ethyl 2-(pyridin-3-ylmethoxy)acetate (600 mg, 66.8%) as colorless oil which was used in next step without further purification. LCMS: 196.1 [M+H]+.

1. stirringthe reaction mixture stirred at 27° C. for further 16 h
2. customthe mixture was quenched by addition of water (50 mL)
3. extractionextracted with ethyl acetate (3×20 mL)
4. washThe combined organic layers were washed with brine (30 mL)
5. dry with materialdried over Na2SO4
6. concentrationconcentrated

ORD record

ord-eee71cce9d034d30bd4cf22290720569

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08940726B2