Triacetoxyperiodinane → 2'-Bromo-5'-isopropoxy-4'-methoxyacetophenone

Participants

Reaction Conditions

Reaction Steps

A magnetically stirred solution of alcohol 37 (520 mg, 1.80 mmol) in CH2Cl2 (10 mL), maintained at 0° C. was treated with Dess-Martin periodinane (1.14 g, 2.69 mmol). The resulting mixture was warmed to 18° C., stirred at this temperature for 2 h then concentrated, under reduced pressure, onto TLC-grade silica (ca. 500 mg). The resulting free-flowing solid was subjected to flash chromatography (1:19 v/v ethyl acetate/hexane elution) to afford the title compound 38 (361 mg, 70%) as a pale-yellow solid, m.p. 59.0-59.9° C., Rf 0.6 in 1:1 v/v ethyl acetate/hexane.

Provenance & Evidence