Triethylamine → 1,1,1-Trifluoro-N-phenylmethanesulfonamide

Participants

Reaction Steps

To a solution of methyl 5-formyl-6-hydroxy-1-naphthoate (500 mg, 2.17 mmol) in CH2Cl2 (10.2 mL) at rt was added Et3N (483 mg, 4.78 mmol, 0.664 mL) followed by PhNTf2 (928 mg, 2.6 mmol). The mixture was stirred for 18 h and then diluted with Et2O and washed with 1.0 M HCl. The extract was dried with MgSO4 and concentrated in vacuo. The crude material was chromatographed on silica gel (20:1 hexanes/EtOAc), and the material thus obtained was recrystallized from hexanes to give 1.0 g of a 3:2 mixture of the title compound and PhNHTf (˜90% yield).

Provenance & Evidence