2-Naphthalenecarboxaldehyde → HCID 59749557, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N,N-dimethyl imidazole-1-sulfonamide (commercially available from Aldrich) (2.0 g, 11.4 mmol) in THF (50 mL) at −78° C. was treated with nBuLi (4.6 mL of a 2.5 M soln) for 1 h. Solid tert-butyl-dimethylsilanyl chloride (TBSCl) (1.72 g, 11.4 mmol) in THF (10 mL) was added at rt for 16 h. The mixture was cooled to −20° C. and treated with nBuLi (4.6 mL of a 2.5 M soln) for 1 h. 2-Naphthaldehyde (1.78 g, 1.1.4 mmol) in THF (10 mL) was added and the mixture was stirred for 3 h at rt. The mixture was washed with brine and dried over Na2SO4. The solvent was removed under vacuum and the residue was purified by chromatography on silical gel with 25% EtOAc:hexane to give 2-(tert-butyl-dimethyl-silanyl)-4-(hydroxy-naphthalen-2-yl-methyl)-imidazole-1-sulfonic acid dimethylamide (Intermediate-I1) 2.6 g (50%).

Provenance & Evidence