Diisobutylaluminum hydride → (R)-(4-azido-3,4-dihydro-2H-chromen-7-yl)methanol

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Reaction Steps

(R)-Methyl 4-azido-3,4-dihydro-2H-chromene-7-carboxylate (21.50 mmol, 1.0 eq) in 50 mL THF was cooled to 0° C., and treated with DIBAL (63.0 mmol, 3.0 eq). After 2.5 h, the reaction mixture was quenched by adding 50% saturated K—Na tartrate (60 mL). After stirring 1 h at room temperature, the solution was extracted with DCM (4×50 mL). The organic layers were then washed with water (2×50 mL), dried over MgSO4 and concentrated. The residue was purified using SiO2 chromatography (10→80% EtOAc/Hexanes) to afford the title compound.

Provenance & Evidence