Formaldehyde → 5-Hydroxymethyl-4-(4-(methylsulfonyl)phenyl)-3-phenyl-2-(5H)-furanone

Participants

Reaction Steps

A mixture of 3-phenyl-4-(4-(methylsulfonyl)phenyl)-2-(5H)-furanone from Step 1 (0.31 g, 1.0 mmol), 37% aqueous formaldehyde solution (0.1 mL), THF (20 mL) and water (5 mL) was treated with K2CO3 (20 mg, 0.15 mmol). After stirring for 1 h at room temperature, the reaction mixture was quenched with 15 mL of saturated aqueous NH4Cl and extracted with 50 mL of EtOAc. The extract was dried over MgSO4 and concentrated. The residue was purified by flash chromatography eluting with 3:1 EtOAc/hexanes to give 50 mg of the title compound along with 120 mg of 5,5-bis(hydroxymethyl)-3-phenyl-4-(4-(methylsulfonyl)phenyl)-2-(5H)-furanone.

Provenance & Evidence