Water → (6-Iodopyridin-3-yl)methanol

Temperature

6 °C

40 g (145 mmol) of ethyl 6-iodonicotinate diluted in 400 mL of ethanol are added dropwise to a solution at 0° C. of 27.3 g (−722 mmol) of sodium borohydride in 270 mL of ethanol. For the addition, the temperature of the reaction mixture is maintained from 2 and 6° C., and then at 0° C. for 1 hour and at room temperature for 20 hours. The reaction is worked up by addition of 200 mL of water, and a white precipitate forms. The reaction mixture is filtered off; the filtrate is evaporated under vacuum to give the product in the form of a yellow paste. The product is placed in 300 mL of diethyl ether and then filtered to give 23.2 g (68%) of (6-iodopyrid-3-yl)methanol in the form of a pale yellow solid.

1. additionFor the addition
2. waitat room temperature for 20 hours
3. filtrationThe reaction mixture is filtered off
4. customthe filtrate is evaporated under vacuum
5. customto give the product in the form of a yellow paste
6. filtrationfiltered

ORD record

ord-47abf3be3189486f97616c720a4c35a6

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08383652B2