Cyclopentadiene → HCID 19428923, compound

HRID 416199Notes

Reaction equation

HRID 416199 reaction equation
[CH:1]1[CH2:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[CH2:9][CH2:10][CH2:11][Si:12]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15]>O1CCCC1>[C:2]1([CH2:9][CH2:10][CH2:11][Si:12]([O:13][CH2:14][CH3:15])([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])[CH2:1][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7612CyclopentadieneHCID 24758Sodium hydrideHCID 78771(3-Chloropropyl)triethoxysilane

Product 1

HCID 19428923HCID 19428923, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

27.5 g (417 mmol) of freshly distilled cyclopentadiene are added dropwise to a suspension of 15 g (417 mmol) of sodium hydride in 250 ml of absolute tetrahydrofuran at room temperature over a period of one hour. 100.3 g of (3-chloropropyl)triethoxysilane are subsequently added dropwise over a period of 30 minutes. The solution becomes warm during this process. After taking off the solvent, the mixture is fractionally distilled in an oil pump vacuum to give 96.1 g of (3-cyclopenta-dienylpropyl)triethoxysilane (yield: 90%).

Workup

  1. temperatureThe solution becomes warm during this process
  2. distillationthe mixture is fractionally distilled in an oil pump vacuum

Sources & evidence

ORD record
ord-14164d67abf74ff6aa33f9703a7c884b
Source dataset
uspto-grants-2012_01
Patent number
US08088878B2

Reaction notes

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