Sodium Bicarbonate → 4-(5-Hydroxy-2-oxo-3-propionyl-2-H-pyran-6-yl)pentanal

Participants

Reaction Conditions

Reaction Steps

4-(5-Hydroxy-2-oxo-3-propionyl-2-H-pyran-6-yl)pentanol (V in Scheme 1; Example 1.4; 0.38 g; 1.5 mmol; Aldrich) was dissolved in 20 ml dichloromethane and 0.6 ml pyridine. Sodium periodinate (0.7 g; 1.65 mmol; Aldrich) was added and stirred for 2 h at 25° C., after which reaction mixture was neutralized with saturated NaHCO3 and extracted with 3×20 ml CH2Cl2. The pooled organic extracts were dried with anhydrous Na2SO4, evaporated, and purified via silica chromatography (20% EtOAc in hexanes).

Provenance & Evidence