ethylcyclopentadiene → HCID 178438266, compound

HRID 735299Notes

Reaction equation

HRID 735299 reaction equation
[BH4-].[Na+].[CH2:3]([C:5]1([Li])[CH:9]=[CH:8][CH:7]=[CH:6]1)[CH3:4].[CH2:11]([C:13]1[CH2:17][CH:16]=[CH:15][CH:14]=1)[CH3:12].C([Li])CCC.[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Ta+5:28]>C1COCC1>[CH2:3]([C:5]1([TaH3:28][C:13]2([CH2:11][CH3:12])[CH:17]=[CH:16][CH:15]=[CH:14]2)[CH:9]=[CH:8][CH:7]=[CH:6]1)[CH3:4]

Participants

7

Reactant 5

HCID 528166ethylcyclopentadieneHCID 4311764Sodium borohydrideHCID 10269745Einecs 254-460-4HCID 178418339ButyllithiumHCID 178506694HCID 178506694, compound

Product 1

HCID 178438266HCID 178438266, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

6.85 g (181 mmol) of sodium borohydride and 40 ml of THF were added to a solution of 48.9 g (489 mmol) of ethylcyclopentadienyl lithium prepared from ethylcyclopentadiene and butyl lithium in THF (200 ml), followed by ice-cooling. 24.9 g (69 mmol) of tantalum pentachloride was added to the mixture, followed by refluxing for 4 hours. The solvent was distilled away in vacuo, and the residue was sublimated at 2.5 Pa/100° C. to obtain 8.80 g (yield: 34.2%) of a white solid.

Workup

  1. temperaturecooling
  2. temperatureby refluxing for 4 hours
  3. distillationThe solvent was distilled away in vacuo
  4. customwas sublimated at 2.5 Pa/100° C.

Sources & evidence

ORD record
ord-b2f3040dfb7a4e78855225c9e59dd5df
Source dataset
uspto-grants-2009_09
Patent number
US07592471B2

Reaction notes

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