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Bis(trimethylsilyl)chloromethane → Bis(trimethylsilyl)methylmethacrylate

HRID 480531
Notes
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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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 552583Bis(trimethylsilyl)chloromethaneHCID 3255932Sodium methacrylate

Product 1

HCID 18764812Bis(trimethylsilyl)methylmethacrylateYield 60%

Reagents, catalysts & solvents 3

HCID 7108PhenothiazineCatalystHCID 21218Trioctylmethylammonium chlorideCatalyst
HCID 6342
Acetonitrile
Solvent

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06653048B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes