Triacetoxyperiodinane → HCID 178501146, compound

Participants

Reaction Steps

To a flask containing methyl trans-4-(hydroxymethyl)cyclohexanecarboxylate (100 mg, 0.581 mmol) in CH2Cl2 (5.8 mL) at 0° C., was added Dess-Martin periodinane (493 mg, 1.16 mmol). The reaction was allowed to warm to room temperature over an hour and then was diluted with EtOAc (60 mL), washed with saturated K2CO3 solution (3×40 mL) and brine (40 mL). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash chromatography on silica gel (0 to 25% EtOAc/hexanes) afforded methyl trans-4-formylcyclohexanecarboxylate. Rf=0.87 (25% EtOAc/hexanes). 1H NMR (CDCl3, 500 MHz) δ 9.63 (s, 1H), 3.67 (s, 3H), 2.51-2.05 (m, 6H), 1.63-1.26 (m, 4H).

Provenance & Evidence