Bromide ion → HCID 57803572, compound

Participants

Reaction Steps

A solution of 5,7-dimethyl-6-(tetrahydro-2H-pyran-2-yloxy)spiro[chroman-2,1′-cyclobutane]-8-carbaldehyde (1.5 g) and triphenylphosphinemethyl bromide (2.5 g) and sodium hydride (400 mg) in DMF (20 mL) was stirred at 40° C. for 5 h. After pouring it into water, it was extracted with ethyl acetate, and the organic layer was dried and evaporated. Then the residue was dissolved in MeOH with dil. HCl and it was stirred at room temperature for 30 min. The mixture was poured into water and extracted with ethyl acetate. The ethyl acetate was washed, dried, and evaporated. The residue was purified by silica gel column eluting with 10% ethyl acetate in hexane, giving 507.7 mg of 5,7-dimethyl-8-vinyl-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-6-ol as a light brown oil.

Provenance & Evidence