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

HRID 1404315Notes

Reaction equation

HRID 1404315 reaction equation
C(N(CC)CC)C.[OH:8][CH:9]1[CH2:14][C:13]([CH3:16])([CH3:15])[NH+:12]([O-:17])[C:11]([CH3:19])([CH3:18])[CH2:10]1.[CH3:20][Si:21](Cl)([CH3:23])[CH3:22]>ClCCl>[CH3:20][Si:21]([CH3:23])([CH3:22])[O:8][CH:9]1[CH2:14][C:13]([CH3:15])([CH3:16])[NH+:12]([O-:17])[C:11]([CH3:19])([CH3:18])[CH2:10]1

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 116079992,2,6,6-tetramethyl-4-hydroxypiperidine-N-oxide

Product 1

HCID 580038804-trimethylsilyloxy-2,2,6,6-tetramethylpiperidine-N-oxideYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

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.

Workup

  1. customa reaction for 2 hours
  2. concentrationit was then concentrated by a rotary evaporator
  3. additionTo the residue 500 ml of water was added
  4. extractionan extraction
  5. concentrationThe organic layer was concentrated by a rotary evaporator
  6. dissolutionthe residue was dissolved in hexane
  7. customrecrystallized

Sources & evidence

ORD record
ord-3e848a84113b4375beeca1718e1f776b
Source dataset
uspto-grants-2014_12
Patent number
US08912287B2

Reaction notes

Loading…