Imidazole → HCID 10991787, compound

Participants

Reaction Steps

To a solution of (S)-5-hydroxy-2-penten-4-olide [3.2 g, 28.07 mmol; prepared from 1,2:5,6-di-O-isopropylidene-D-mannitol (Aldrich) in a 3-step sequence described by Hafele and Jager in Liebigs Ann. Chem. 1987, 85-87], in dry DMF (50 ml), at 0° C., was added imidazole (2.95 g, 42.1 mmol), followed by tert-butylchlorodiphenylsilane (7.95 ml, 30.9 mmol). The cooling bath was removed and the reaction mixture was stirred at room temperature for a period of 1 h. Then, the solvent was evaporated and the residue was purified on a silica gel column using hexane/EtOAc (7:3 v/v) as the eluent. The appropriate fractions were evaporated and gave 9.0 g (91%) of MSC-006. 13C-NMR (CDCl3)δ: 19.40, 26.88, 63.53, 83.40, 122.89, 128.05, 130.20, 132.68, 132.95, 135.71, 135.76, 154.20. (The carbonyl carbon was not detected).

Provenance & Evidence