Imidazole → HCID 89287803, compound

Participants

Reaction Steps

To a solution of 5-chloro-4-(4-ethoxybenzyl)-2-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((5-hydroxypentyloxy)methyl)tetrahydro-2H-pyran-2-yl)phenol (30, 459 mg, 0.58 mmol) in benzene (3 mL) under an atmosphere of nitrogen were added imidazole (448 mg, 1.76 mmol) and triphenylphosphine (467 mg, 1.76 mmol). After 5 min, iodine (448 mg, 1.76 mmol) in benzene (2 mL) was added dropwide to the reaction mixture at room temperature. The reaction solution was stirred for 1 h, diluted with diethyl ether, quenched with saturated sodium hydrogen carbonate, extracted with diethyl ether (2×). The organic layer was washed with brine, dried over magnesium sulfate, filtered and evaporated in vacuo. The resulting crude residue was purified on a Biotage® purification apparatus (silica gel, 5 to 25% tetrahydrofuran in hexanes gradient) to yield the title compound (31, 485 mg, 0.54 mmol, 93%) as yellow foam.

Provenance & Evidence