Sodium Thiosulfate → 9-Hydroxy-5,9-dimethyl-decanal

Participants

Reaction Steps

To a stirred solution of diol 14 (25 mg, 0.12 mmol) in anhydrous CH2Cl2 (3.5 mL) was added Dess-Martin reagent (73 mg, 0.15 mmol) at room temperature. The reaction was stirred at room temperature for 1.5 hours. Then, an aqueous solution of sodium thiosulfate (6 mL) and saturated NaHCO3 (6 mL) were added. The reaction was extracted with CH2Cl2, solvents were removed under reduced pressure, and the crude oil was purified on silica Sep-Pak using hexane/EtOAc (7:3) as an eluent to give an oily aldehyde 15 (16.5 mg, 67%).

Provenance & Evidence