Bis(trimethylsilyl)chloromethane → Bis(trimethylsilyl)methylmethacrylate

HRID 480531

Reaction equation

HRID 480531 reaction equation
[CH3:1][Si:2]([CH:5]([Si:7]([CH3:10])([CH3:9])[CH3:8])Cl)([CH3:4])[CH3:3].[C:11]([O-:16])(=[O:15])[C:12]([CH3:14])=[CH2:13].[Na+]>CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].C1C2NC3C(=CC=CC=3)SC=2C=CC=1.C(#N)C>[CH3:1][Si:2]([CH:5]([O:16][C:11](=[O:15])[C:12]([CH3:14])=[CH2:13])[Si:7]([CH3:10])([CH3:9])[CH3:8])([CH3:4])[CH3:3]

Participants

6

Reactant 2

HCID 552583Bis(trimethylsilyl)chloromethaneHCID 3255932Sodium methacrylate

Product 1

HCID 18764812Bis(trimethylsilyl)methylmethacrylateYield 60%

Reagents, catalysts & solvents 3

HCID 7108PhenothiazineCatalystHCID 21218Trioctylmethylammonium chlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

Bis(trimethylsilyl)chloromethane (Aldrich) (14.68 g, 0.075 mole), sodium methacrylate (8.96 g, 0.0825 mole), Adogen 464 (Aldrich) (1.70 g), and phenothiazine (0.05 grams) were placed in a round bottom flask equipped with a condenser, mechanical stirrer and a nitrogen inlet. The flask was charged with 200 ml acetonitrile and heated to reflux while stirring. After 4 days, the mixture was filtered to remove the solids and the solvent was removed in a rotary evaporator. Fractional distillation under reduced pressure gave 10.90 grams (60% yield) of a clear liquid at 46-48° C. at 0.5 mm pressure.

Workup

  1. customequipped with a condenser, mechanical stirrer and a nitrogen inlet
  2. temperatureheated
  3. temperatureto reflux
  4. filtrationthe mixture was filtered
  5. customto remove the solids
  6. customthe solvent was removed in a rotary evaporator
  7. distillationFractional distillation under reduced pressure

Sources & evidence

ORD record
ord-de947e5f70ac4014a4c75f782fec3f15
Source dataset
uspto-grants-2003_11
Patent number
US06653048B2

Linked notes

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