Diisobutylaluminum hydride → 2,2-Dimethylspiro[chroman-4,1'-cyclopropane]-6-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

Methyl 2,2-dimethyl-2,3-dihydrospiro[chromene-4,1′-cyclopropane]-6-carboxylate (33.0 mg, 0.13 mmol) was dissolved in dry toluene (1.34 mL), and cooled to −78° C. DIBAL-H (536 μL, 0.54 mmol) was added dropwise via a syringe. The reaction mixture was stirred for 2 hours at −78° C. It was then quenched with methanol (500 μL) at the same temperature, and diluted with EtOAc (15.0 mL). The organic layer was washed with water (10.0 mL), dried over Na2SO4, filtered and concentrated under vacuum to afford the crude alcohol, which was used directly to the next step. The crude alcohol was dissolved in dichloromethane (4.00 mL) and Dess-Martin periodinane (114 mg, 0.27 mmol) was added in one portion at room temperature. The resulting mixture was stirred at room temperature for 1 hour and concentrated under vacuum on silica gel. It was then purified by silica gel chromatography eluting with 0-15% EtOAc/hexanes to give the desired product as a colorless oil.

Provenance & Evidence