Chlorotrimethylsilane → 4-trimethylsilyloxy-2,2,6,6-tetramethylpiperidine-N-oxide

Participants

Reaction Conditions

Reaction Steps

To a solution in which 48.6 g (480 mmol) of triethylamine and 68.9 g (400 mmol) of 4-hydroxy-2,2,6,6-tetramethylpiperidine-N-oxide (TEMPOL) were dissolved in 100 mL of di-chloromethane, 47.8 g (440 mmol) of trimethylsilyl chloride was added at 0° C. The temperature was raised to 25° C. to carry out a reaction for 2 hours, and it was then concentrated by a rotary evaporator. To the residue 500 ml of water was added, and an extraction was carried out using 500 ml in total of ethyl acetate. The organic layer was concentrated by a rotary evaporator and the residue was dissolved in hexane and recrystallized to obtain 96.2 g of 4-trimethylsilyloxy-2,2,6,6-tetramethylpiperidine-N-oxide.

Provenance & Evidence