Sodium Iodide → p-Nitrobenzyl 2-diazo-3-trimethylsilyloxy-3-butenoate

Participants

Reaction Steps

To 1.5 ml of dry acetonitrile were added 100 mg (0.380 millimole) of p-nitrobenzyl 2-diazoacetoacetate, 64.8 μl (0.465 millimole) of triethylamine and 59 μl (0.465 millimole) of trimethylsilyl chloride. A solution obtained by dissolving 70 mg (0.467 millimole) of sodium iodide in 0.5 ml of dry acetonitrile was added dropwise thereto at a room temperature. After agitation for an hour, the reaction mixture was concentrated under a reduced pressure. After addition of 5 ml of hexane, insoluble materials were filtered off and the hexane was distilled off under a reduced pressure to give 115 mg (yield 90.1 %) of the desired compound in a yellow solid.

Provenance & Evidence