Imidazole → HCID 68466455, compound

Participants

Reaction Steps

6N-benzoyl-8-bromo-5′-O-(4,4′-dimethoxytrityl)-2′-deoxyadenosine (Compound 2) (14 gm, 19 mmol) and imidazole (1.94 gm, 28.5 mmol) were dissolved in 100 mL of dry DMF and t-butyldimethyl-silyl chloride (4.3 gm, 28.5 mmol) added to the stirring solution at room temperature. After 4 hrs, TLC on silica gel (2.5% MeOH in CH2Cl2) showed that all starting material had been converted to a new product with higher Rf. The solution was concentrated into a small volume, then about 400 mL of ether was added and washed three times with saturated aqueous NaCl solution. The organic layer was dried over anhydrous Na2SO4, and the filtrate was evaporated to give an off-white foamy product (16.18 gm, 100%). HNMR and ES-MS confirmed the structure.

Provenance & Evidence