Water → 2,1-Benzisothiazole-4-methanol

To a solution of methyl 2,1-benzisothiazole-4-carboxylate (5.00 g, 25.9 mmol) in tetrahydrofuran (129 mL) was added diisobutylaluminum hydride (1 M hexane solution, 78.0 mL, 78.0 mmol) at −78° C., and the mixture was stirred at room temperature for 3 hr. The reaction solution was cooled to 0° C., and water was added. The mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80) to give the title compound (4.2 g, yield 98%).

1. temperatureThe reaction solution was cooled to 0° C.
2. extractionThe mixture was extracted with ethyl acetate
3. washwashed with saturated brine
4. dry with materialdried over anhydrous sodium sulfate
5. customthe solvent was evaporated under reduced pressure
6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80)

ORD record

ord-331d46093efd4e009b397c577a85067e

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08110585B2