Triacetoxyperiodinane → 2,2-Dimethyl-3-(3-methylcyclohexyl)propanal

Participants

Reaction Conditions

Reaction Steps

A solution of Dess Martin periodinane (9.0 g, 21.1 mmol, 1.3 eq) in dichloromethane (165 mL) was charged into a 250 mL three-necked round-bottom flask, equipped with a mechanical stirrer and a reflux condenser. The solution was cooled to 0° C. by the mean of an ice/salt bath. 2,2-dimethyl-3-(3-methylcyclohexyl)propan-1-ol (3.0 g, 16.3 mmol) was added dropwise. After stirring for 2 h at ambient temperature, the mixture was cooled down to −15° C. and the solid was filtered off. The organic solution was then concentrated. The resultant crude product was chromatographed on a silica gel column with 2% EtOAc in hexane as elution agent giving 2,2-dimethyl-3-(3-methylcyclohexyl)propanal (1.0 g, gc purity>85%; yield 33%).

Provenance & Evidence