2-Chloroethyl methyl ether → HCID 18704298, compound

HRID 480994Notes

Reaction equation

HRID 480994 reaction equation
[CH3:1][O:2][CH2:3][CH2:4]Cl.[CH3:6][Si:7]([C:10]1([Na])[CH:14]=[CH:13][CH:12]=[CH:11]1)([CH3:9])[CH3:8]>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][C:11]1[CH:12]=[CH:13][CH2:14][C:10]=1[Si:7]([CH3:9])([CH3:8])[CH3:6]

Participants

4

Reactant 2

HCID 123162-Chloroethyl methyl etherHCID 178504167HCID 178504167, compound

Product 1

HCID 18704298HCID 18704298, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of 18.9 g (200 mmol) of chloroethyl methyl ether in 100 ml of THF was gradually dropwise added to a solution of 32 g (200 mmol) of trimethylsilyl-cyclopentadienylsodium in 400 ml of THF while being stirred in an argon atmosphere at −78° C. After completion of the addition, the reaction mixture was heated under reflux overnight. Then THF was distilled off under a reduced pressure, and the obtained solid was filtered off and subjected to vacuum distillation (80° C./1 mmHg) to give about 33 g of [(2-methoxy)ethyl]-trimethylsilylcyclopentadiene (TMSCpCH2CH2OMe). Yield: 85%. The chemical structure was confirmed by the following data obtained by 1H-NMR using CDCl3.

Workup

  1. additionAfter completion of the addition
  2. temperaturethe reaction mixture was heated
  3. temperatureunder reflux overnight
  4. distillationThen THF was distilled off under a reduced pressure
  5. filtrationthe obtained solid was filtered off
  6. distillationsubjected to vacuum distillation (80° C./1 mmHg)

Sources & evidence

ORD record
ord-3b34aef9213e473baf221a190ab41f65
Source dataset
uspto-grants-2003_11
Patent number
US06653430B1

Reaction notes

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