Ethyl bromoacetate → Ethyl 2-(tetramethylcyclopentadienyl)acetate

HRID 434123Notes

Reaction equation

HRID 434123 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:8][C:9]1[CH-:13][C:12]([CH3:14])=[C:11]([CH3:15])[C:10]=1[CH3:16].[Na+]>C1COCC1>[CH3:8][C:9]1[CH:13]([CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:12]([CH3:14])=[C:11]([CH3:15])[C:10]=1[CH3:16]

Participants

4

Reactant 2

HCID 7748Ethyl bromoacetateHCID 15823254Tetramethylcyclopentadienylsodium

Product 1

HCID 85614880Ethyl 2-(tetramethylcyclopentadienyl)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3.822 g (22.89 mmol) ethyl bromoacetate in 25 mL THF was cooled to −78° C. and 3.000 g (20.80 g) sodium tetramethylcyclopentadienide in 50 mL THF was slowly added to it. The resulting slurry was allowed to warm to room temperature and was stirred overnight. The solvent was removed, the residue was extracted with pentane and filtered. The pentane was removed to give a mixture of isomers. Yield was 3.733 g (86.3%). Mass spectra m/e 208 (41 percent).

Workup

  1. customThe solvent was removed
  2. extractionthe residue was extracted with pentane
  3. filtrationfiltered
  4. customThe pentane was removed
  5. customto give
  6. additiona mixture of isomers

Sources & evidence

ORD record
ord-806da6fc76fa438c8340b5aede2b1f8e
Source dataset
uspto-grants-2003_12
Patent number
US06670432B1

Reaction notes

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