Tetrahydrofuran → (6-Chloropyridin-3-yl)methanol

To a mixture of 3.0 g (0.0175 mole) of methyl 6-chloronicotinate, 2.0 g of sodium borohydride and 60 ml of THF on reflux, 8.0 ml of MeOH was added with stirring over a period of 1 hour. After completion of the dropwise addition, the mixture was further refluxed for 30 minutes and when cold, the solvent was distilled off. The residue was diluted with 30 ml of water, saturated with NaCl and extracted with CH2Cl2 (20 ml×3). The CH2Cl2 layer was dried over MgSO4 and the CH2Cl2 was distilled off to give 2.3 g of 6-chloro-3-pyridylmethanol as a yellow oil. When left standing at room temperature, this product was thoroughly crystallized.

1. temperatureon reflux
2. additionAfter completion of the dropwise addition
3. temperaturethe mixture was further refluxed for 30 minutes
4. distillationwhen cold, the solvent was distilled off
5. additionThe residue was diluted with 30 ml of water, saturated with NaCl
6. extractionextracted with CH2Cl2 (20 ml×3)
7. dry with materialThe CH2Cl2 layer was dried over MgSO4
8. distillationthe CH2Cl2 was distilled off

ORD record

ord-51134f8625c64e248dbb22e63b7535bd

Source dataset

uspto-grants-1992_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05175301