HCID 4935483, compound → HCID 11086797, compound

Participants

Reaction Steps

A methanolic (700 mL) solution of compound 2 (29 g, 115 mmol) was cooled in an ice bath before the addition of bis(acetoxyiodo) benzene (62 g, 194 mmol) in six portions over a period of 30 minutes. The solution was stirred in the ice bath for 2 hours then brought to room temperature and stirred overnight. The reaction mixture was diluted with ethyl acetate (1.5 L) and rinsed with water, dilute hydrochloric acid, and brine. The aqueous was back-extracted once with ethyl acetate and the organics combined before drying over anhydrous magnesium sulfate, followed by filtration, and solvent evaporation. The resulting liquid was purified over silica gel using a gradient of ethyl acetate (0 to 2%) in heptane, giving 6.9 g (21%) (3) as a yellow-orange solid. Material was sufficiently pure (approx. 95%) by 1H NMR, which was consistent with that reported in the literature (Synthesis 1998, 775).

Provenance & Evidence