Diisobutylaluminum hydride → HCID 77230775, compound

Temperature

-78 °C

Methyl 4-cyclopropyl-2H-chromene-6-carboxylate (101 mg, 0.44 mmol) was dissolved in dichloromethane (4.40 mL), and cooled to −78° C. DIBAL-H (877 μL, 0.88 mmol) was added dropwise. The reaction mixture was stirred for 2 hours at −78° C. and warmed to room temperature. It was then quenched with methanol at room temperature and diluted with dichloromethane. The organic layer was washed with water, dried over Na2SO4, filtered and concentrated under vacuum. The crude residue was used directly in the next step. The crude alcohol was dissolved in dichloromethane (4.00 mL) and Dess-Martin periodinane (372 mg, 0.88 mmol) was added in one portion at room temperature. The mixture was stirred at room temperature for 1 hour and concentrated under vacuum on silica gel. The crude residue was purified by silica gel chromatography eluting with 0-20% EtOAc/Hexanes to afford the desired product as a colorless oil.

1. temperaturewarmed to room temperature
2. customIt was then quenched with methanol at room temperature
3. additiondiluted with dichloromethane
4. washThe organic layer was washed with water
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated under vacuum
8. dissolutionThe crude alcohol was dissolved in dichloromethane (4.00 mL)
9. stirringThe mixture was stirred at room temperature for 1 hour
10. concentrationconcentrated under vacuum on silica gel
11. customThe crude residue was purified by silica gel chromatography
12. washeluting with 0-20% EtOAc/Hexanes

ORD record

ord-781b9f8eb10b4e27817b0c3f6f5b10f2

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08742110B2