Chloroform → 3,5-Dioxohexanoic acid

Participants

Reaction Steps

A suspension of 5-cyanomethyl-1-β-D-ribofuranosylimidazole-4-carboxamide (1.41 g, 5 mmol), acetic anhydride (15 ml) and p-dimethylaminopyridine (20 mg) was stirred at RT for 8 hr. Tlc (silica gel, CHCl3 --MeOH, 4:1) indicated three products. Additional p-dimethylaminopyridine (20 mg) and acetic anhydride (5 ml) was added and stirring continued at RT for 36 hr. The solution was evaporated in vacuo to a syrup which was dissolved in chloroform and placed on a column of silica gel (60 g). Elution with chloroform-methanol (20:1) provided the triacetate (2.0 g, 95%) as a white foam; pmr (DMSO-d6): δ 2.08, 2.10, 2.16 (s,3,COCH3), 4.40 (s,2,CH2), 6.13 (d,1,H1'), J = 5Hz, 7.39, 7.58 (s,2,NH), 8.19 (s,1,C2H).

Provenance & Evidence