Phenol → HCID 86620289, compound

Participants

Reaction Conditions

Reaction Steps

The substrate phenol or carboxylic acid is dissolved in THF (0.05-0.5 M) and chilled to 0° C. Triphenylphosphine (1 -4 eq), alcohol (1-4 eq) and duisopropyl azodicaroxylate (DIAD) or diethyl azodicarboxylate (DEAD) (1 -4 eq) were added, in turn. The reaction was stirred overnight with gradual warming to rt. The reaction mixture is diluted with EtOAc/water and the layers were separated. The aqueous layer is further extracted with EtOAc. The organic layers were combined and washed with water and brine and dried over Na2SO4. The mixture is concentrated in vacuo to give the crude product, which was purified by flash chromatography on silica gel to afford the coupling product.

Provenance & Evidence