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. additionwas dropwise added at −30° C.
2. customto give rise
3. customto a reaction
4. additionwas added to the reaction mixture
5. extractionfollowed by extraction with ethyl acetate
6. washThe resulting organic layer was washed with water
7. dry with materialan aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate
8. distillationThe resulting solution was subjected to vacuum distillation
9. customto remove the solvent
10. customThe residue was purified by silica gel column chromatography

ORD record

ord-708e5fbf745745f2b46ec28bd2327e28

Source dataset

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07238689B2