2-Allyl-2-chloro-4,4,5,5-tetramethyl-[1,3,2]dioxasilolane → 2-Allyl-4,4,5,5-tetramethyl-2-vinyloxy-[1,3,2]dioxasilolane

HRID 493459Notes

Reaction equation

HRID 493459 reaction equation
[Li]C.[CH3:3][C:4]([O:8][SiH3])=C(C)C.[CH2:10]([Si:13]1(Cl)[O:17][C:16]([CH3:19])([CH3:18])[C:15]([CH3:21])([CH3:20])[O:14]1)[CH:11]=[CH2:12]>CCCCC>[CH2:10]([Si:13]1([O:8][CH:4]=[CH2:3])[O:17][C:16]([CH3:19])([CH3:18])[C:15]([CH3:21])([CH3:20])[O:14]1)[CH:11]=[CH2:12]

Participants

5

Reactant 3

HCID 576817222-Allyl-2-chloro-4,4,5,5-tetramethyl-[1,3,2]dioxasilolaneHCID 101265072TrimethylvinyloxysilaneHCID 178418348HCID 178418348, compound

Product 1

HCID 111955422-Allyl-4,4,5,5-tetramethyl-2-vinyloxy-[1,3,2]dioxasilolaneYield 72.3%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

To a cooled (0° C.) solution of MeLi (16.2 mL; 23 mmol; 1.4 M in Et20) was added trimethylvinyloxysilane (2.7 g; 23 mmol). The solution was warmed to room temperature and was stirred for 1 hour. The solution was cooled to −78° C., and 2-allyl-2-chloro-4,4,5,5-tetramethyl-[1,3,2]dioxasilolane (5.5 g; 25 mmol) was added. The solution was warmed to room temperature and stirred for 2 hours. The solution was diluted with pentane (20 mL), and the mixture was then filtered through a pad of celite. The filtrate was concentrated, and the residue was distilled under reduced pressure to give 3.8 g (70%) of 2-allyl-4,4,5,5-tetramethyl-2-vinyloxy-[1,3,2]dioxasilolane as a clear, colorless liquid.

Workup

  1. temperatureThe solution was cooled to −78° C.
  2. temperatureThe solution was warmed to room temperature
  3. stirringstirred for 2 hours
  4. filtrationthe mixture was then filtered through a pad of celite
  5. concentrationThe filtrate was concentrated
  6. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-39a427f8a7a24e40bba5fb4f4b9d73fc
Source dataset
uspto-grants-2009_05
Patent number
US07534905B2

Reaction notes

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