Water → HCID 17862916, compound

Temperature

-20 °C

A solution of 1.9 g (10.0 mmoles) of methyl 2-chloro-4-methylnicotinate dissolved in 5.0 ml of THF was gradually added, at −65 to −60° C., to a suspension of 0.4 g (10.0 mmoles) of lithium aluminum hydride in 30 ml of tetrahydrofuran. The mixture was stirred for 30 minutes and at −20° C. for 1 hour to give rise to a reaction. The reaction mixture was poured into water, followed by extraction with ethyl acetate. The resulting organic layer was washed with water and an aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein. The residue was purified by silica gel column chromatography to obtain 0.6 g (yield: 38.2%) of (2-chloro-4-methylpyridin-3-yl)methanol.

1. customto give rise
2. customto a reaction
3. extractionfollowed by extraction with ethyl acetate
4. washThe resulting organic layer was washed with water
5. dry with materialan aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate
6. distillationThe resulting solution was subjected to vacuum distillation
7. customto remove the solvent
8. customThe residue was purified by silica gel column chromatography

ORD record

ord-8e4f69a4015244c984571d40bbe54b4c

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07833939B2