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

Participants

Reaction Steps

Into 5 ml of dry acetonitrile were suspended 263 mg (1 millimole) of p-nitrobenzyl 2-diazoacetoacetate and 210 mg (1.4 millimoles) of sodium iodide. To the mixture were added 220 μl (1.6 millimoles) of triethylamine and then 190 μl (1.5 millimoles) of trimethylsilyl chloride while agitating in an argon atmosphere at a room temperature. After the resulting orange suspension was agitated at a room temperature for an hour, it was concentrated under a reduced pressure. To the residue was added 20 ml of dry hexane, and the resultant was agitated for 30 min. at a room temperature. Insoluble materials were removed by filtration and the hexane solution was concentrated to dryness under a reduced pressure to give 330 mg (yield 98 %) of the desired compound in a yellow solid. The physical properties of the product were in agreement with those of the product obtained in Example 1.

Provenance & Evidence