Toluene → 1-(Trimethylsilyl)pyrrolidin-2-one

HRID 727536Notes

Reaction equation

HRID 727536 reaction equation
Cl[Si:2]([CH3:5])([CH3:4])[CH3:3].[NH:6]1[CH2:10][CH2:9][CH2:8][C:7]1=[O:11].C(N(CC)CC)C.C1(C)C=CC=CC=1>CCCCCC>[CH3:3][Si:2]([CH3:5])([CH3:4])[N:6]1[CH2:10][CH2:9][CH2:8][C:7]1=[O:11]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 120252-Pyrrolidone

Product 1

HCID 844611-(Trimethylsilyl)pyrrolidin-2-oneYield 94%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Chlorotrimethylsilane (TMSCl, 56.0 mL, 441 mmol) is added dropwise to a solution of 2-pyrrolidinone (30.4 mL, 400 mmol), triethylamine (70.0 mL, 502 mmol) and toluene (400 mL) at room temperature. After stirring at room temperature with a mechanical stirrer for 20 minutes, the mixture is heated at 50° C. for 4 hours. After cooling, the mixture is diluted with hexane (300 mL) and stirred for 30 minutes at room temperature. The mixture is filtered and the filtrate concentrated. Distillation of the residue (1 mm, 68+-74° C.) gives 50.0 g (94%) of the title compound as an oil.

Workup

  1. temperaturethe mixture is heated at 50° C. for 4 hours
  2. temperatureAfter cooling
  3. stirringstirred for 30 minutes at room temperature
  4. filtrationThe mixture is filtered
  5. concentrationthe filtrate concentrated
  6. distillationDistillation of the residue (1 mm, 68+-74° C.)

Sources & evidence

ORD record
ord-267b520ff6e9472f915a68ce24d1ec78
Source dataset
uspto-grants-1998_01
Patent number
US05712300

Reaction notes

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