Borane → (4-(Ethylsulfonyl)phenyl)methanol

Temperature

70 °C

To a stirring solution of 4-(ethylsulfonyl)benzoic acid (500 mg, 2.33 mmol) in THF (5 mL) at 0° C. under argon was added 1 M borane in THF solution (3.5 mL, 3.5 mmol). The reaction mixture was stirred at 70° C. for 20 min. The reaction mixture was then cooled to room temperature, and the THF was removed under reduced pressure. The residue thus obtained was diluted with methanol (5 mL) and stirred for 5 min. Methanol was then removed under reduced pressure. This process was repeated two more times to ensure complete methanolysis of any borane complex. After residual solvent removal under vacuum, 420 mg of the title compound was obtained as a colorless gum. HPLC/MS: retention time=1.373 min, [M+H]+=201.

1. temperatureThe reaction mixture was then cooled to room temperature
2. customthe THF was removed under reduced pressure
3. customThe residue thus obtained
4. stirringstirred for 5 min
5. customMethanol was then removed under reduced pressure
6. customAfter residual solvent removal under vacuum

ORD record

ord-d999d6f4c208429790aff61f185a47d5

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07452892B2