Diisobutylaluminum hydride → HCID 77230775, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence