2-Chloroethanol → 2-(Pyridin-3-yloxy)ethan-1-ol

Temperature

130 °C

A mixture of 3-hydroxypyridine (2.00 g, 21 mmol), 2-chloroethanol (1.69 g, 21 mmol) and K2CO3 (8.7 g, 63 mmol) in DMF (10 mL) was stirred at 130° C. for 3 h. After cooling, the black mixture was filtered through a short bed of alumina using acetone as eluent to afford a brown oil which was partitioned between water (30 mL) and CH2Cl2 (40 mL). The aqueous phase was extracted with CH2Cl2 (3×40 mL), and the combined organic extracts were dried over MgSO4 and filtered. The filtrate was concentrated to give 0.55 g (19%) of the title compound as a light brown oil. Anal. (C7H9NO2.0.2 H2O) C, H, N.

1. temperatureAfter cooling
2. filtrationthe black mixture was filtered through a short bed of alumina
3. customto afford a brown oil which
4. customwas partitioned between water (30 mL) and CH2Cl2 (40 mL)
5. extractionThe aqueous phase was extracted with CH2Cl2 (3×40 mL)
6. dry with materialthe combined organic extracts were dried over MgSO4
7. filtrationfiltered
8. concentrationThe filtrate was concentrated

ORD record

ord-15c6255e56044daf9adf8785fdc5501f

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06465467B1