Methanol → 2-(1,2-Benzoxazol-3-yl)ethan-1-ol

To a solution of benzo[d]isoxazol-3-yl-acetic acid (0.86 g, 4.85 mmol) in anhydrous THF (40 mL) was added dropwise borane dimethylsulfide complex (0.58 mL, 10 M, 5.8 mmol) at 0° C. The mixture was allowed to warm to room temperature and was stirred over night. MeOH (10 mL) was carefully added and when the gas evolution ceased, the mixture was heated under gentle reflux for 4 hours. The reaction mixture was concentrated in vacuo and the remainder was dissolved in dichloromethane (20 mL). An aqueous solution of Na2CO3 (20 mL) was added and the aqueous layer was extracted with dichloromethane (3×20 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The crude product was purified by chromatography on silica gel which afforded 537 mg (67.8%) of the title compound.

1. temperaturethe mixture was heated
2. temperatureunder gentle reflux for 4 hours
3. concentrationThe reaction mixture was concentrated in vacuo
4. dissolutionthe remainder was dissolved in dichloromethane (20 mL)
5. additionAn aqueous solution of Na2CO3 (20 mL) was added
6. extractionthe aqueous layer was extracted with dichloromethane (3×20 mL)
7. dry with materialThe combined organic layers were dried over Na2SO4
8. concentrationconcentrated in vacuo
9. customThe crude product was purified by chromatography on silica gel which

ORD record

ord-45732593fc904a91afdf11f47f27f929

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07648985B2