Water → HCID 68289805, compound

To a solution of 7-chloro-1-benzothiophene-2-carboxylic acid (synthesized by the method of Journal of Chemical Society Perkin Trans. 1, 1984, 385, 1.00 g, 4.70 mmol) in tetrahydrofuran (17 mL) was added a solution of 0.95 mol/L borane-tetrahydrofuran complex in tetrahydrofuran (9.90 mL, 9.41 mmol) at 0° C. The mixture was stirred at room temperature overnight, and then to the reaction solution was added water, and the mixture was concentrated under reduced pressure to remove solvent. To the resulting residue was added saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate twice. The organic layer was combined, washed with water and saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was washed with hexane-diisopropyl ether to give (7-chloro-1-benzothien-2-yl)methanol (842 mg, 90%) as a colorless powder.

1. concentrationthe mixture was concentrated under reduced pressure
2. customto remove solvent
3. additionTo the resulting residue was added saturated aqueous sodium hydrogen carbonate solution
4. extractionthe mixture was extracted with ethyl acetate twice
5. washwashed with water and saturated brine
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated under reduced pressure
8. washThe resulting residue was washed with hexane-diisopropyl ether

ORD record

ord-bef1d2fed9f14e5693cf05f4468ee84e

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987445B2