Ammonium Chloride → 1-(Furo[2,3-c]pyridin-5-yl)ethanol

Temperature

0 °C

5-Acetylfuro[2,3-c]pyridine obtained in Example 4(2.42 g, 15.0 mmol) was dissolved in toluene (30 mL), and the solution was cooled to 0° C. To the cooled solution,16.0 mL (16.0 mmol) of 1.0 M solution of diisobutyl aluminum hydride in toluene solution was added, and the solution was stirred for 2 hours at the same temperature, the reaction mixture was then poured into 100 mL of a 5% ammonium chloride aqueous solution which had been cooled on ice, and it was extracted twice with 100 mL of ethyl acetate. After washing with 100 mL of saturated sodium bicarbonate aqueous solution and 100 mL of saturated saline water, the extract was concentrated to give 2.36 g of crude product. This product was purified by column chromatography on silica gel, giving 2.25 g (92.0% yield) of 5-(1-hydroxyethyl)furo[2,3-c]pyridine.

1. temperaturehad been cooled on ice, and it
2. extractionwas extracted twice with 100 mL of ethyl acetate
3. washAfter washing with 100 mL of saturated sodium bicarbonate aqueous solution and 100 mL of saturated saline water
4. concentrationthe extract was concentrated
5. customto give 2.36 g of crude product
6. customThis product was purified by column chromatography on silica gel

ORD record

ord-c2a9d38b59df4137a03d4b9cd0c90fea

Source dataset

uspto-grants-2002_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06342606B2