Toluene → HCID 18694138, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of intermediate (4-a) (0.11 mol) in tetrahydrofuran (250 ml) was stirred under nitrogen flow. 1,1'-Carbonylbis-1H-imidazole (0.11 mol) was added and the reaction mixture was stirred for 2 hours at room temperature. Then, it was cooled to -80° C. A solution of diisobutylaluminum hydride in methyl benzene (20%) (0.33 mol) was added dropwise and the reaction mixture was stirred for 2 hours at -80° C. The mixture was decomposed with methanol, then poured out into water. The mixture was acidified, then extracted with 1,1'-oxybisethane. The separated organic layer was dried (MgSO4), filtered and the solvent was evaporated, yielding 12 g of (±)-2,3,4,7,8,9-hexahydrocyclopenta[h]-1-benzopyran-2-carboxaldehyde (interm. 5-a).

Provenance & Evidence