Triacetoxyperiodinane → Tert-butyl 1-formylcyclopropane-1-carboxylate

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Reaction Steps

Step 3 To a stirred suspension of tert-butyl 1-(hydroxymethyl)cyclopropane-1-carboxylate (0.16 g, 0.929 mmol) and sodium hydrogen carbonate (0.312 g, 3.72 mmol) in DCM (5.57 mL) at room temperature was added Dess-Martin periodinane (0.788 g, 1.86 mmol). The mixture was stirred at room temperature for 1 hour before it was quenched by the addition of a 1:1 mixture of saturated NaHCO3 solution and saturated Na2S2O3 solution. After stirring for an additional 1 hour the phases were separated and the aqueous phase was extracted into DCM (×2). Combined organic extracts were dried (Na2SO4), filtered and concentrated giving tert-butyl 1-formylcyclopropane-1-carboxylate which was used without further purification, 0.141 g.

Provenance & Evidence