Water → (5-Chloro-3-methyl-isothiazol-4-yl)-methanol

A solution of 2.06 g (10.0 mmoles) of ethyl 5-chloro-3-methyl-isothiazole-4-carboxylate dissolved in 10 ml of THF was dropwise added, at −30° C., to a solution of 0.42 g (11.0 mmoles) of lithium aluminum hydride dissolved in 10 ml of THF. The mixture was stirred at the same temperature for 1 hour to give rise to a reaction. After confirmation of the completion of the reaction, ethyl acetate was added to the reaction mixture. The resulting 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 1.50 g (yield: 91.5%) of (5-chloro-3-methyl-isothiazol-4-yl)-methanol.

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

ORD record

ord-90cb5a03027240098e80dba4e167f706

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07833939B2