Diethyl Ether → HCID 18794596, compound

Participants

Reaction Steps

Dess-Martin reagent (1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one, 3.0 g, 4.8 mmol) was added to a solution of the title D compound 3 (1.1 g, 3.2 mmol) in CH2Cl2 (20 mL) stirring under argon at ambient temperature in a flame-dried flask. After stirring at ambient temperature for 1.8 hours, ether was added and the reaction evaporated in vacuo. The residue was transferred to a separatory funnel with ether (200 mL) and 1/1 10% Na2S2O3 /saturated NaHCO3 (150 mL). Extraction with ether and washing with water (50 mL) and brine (50 mL) and drying over MgSO4 afforded 1.1 g of crude product. Flash chromatography (silica gel, 10% EtOAc/hexane) afforded 0.80 g (72%) yield of compound 6: Rf (silica, 15% EtOAc/hexane)=0.45.

Provenance & Evidence