Bis(eta-cyclopentadienyl) iron → HCID 178520624, compound

HRID 1658893Notes

Reaction equation

HRID 1658893 reaction equation
[C:1]([CH2:9][CH2:10][CH2:11][C:12](Cl)=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH-:15]1[CH:19]=[CH:18][CH:17]=[CH:16]1.[CH-:20]1[CH:24]=[CH:23][CH:22]=[CH:21]1.[Fe+2:25].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[C:1]([CH2:9][CH2:10][CH2:11][C:12]([C-:15]1[CH:19]=[CH:18][CH:17]=[CH:16]1)=[O:13])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH-:20]1[CH:24]=[CH:23][CH:22]=[CH:21]1.[Fe+2:25]

Participants

5

Reactant 3

HCID 7611Bis(eta-cyclopentadienyl) ironHCID 6451240Aluminum(III) ChlorideHCID 12692055HCID 12692055, compound

Product 1

HCID 178520624HCID 178520624, compoundYield 3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Benzoylbutryl chloride (assumed to be 0.005 mole) and ferrocene (0.97g; 0.005 mole) in dry methylene chloride (25 ml) were stirred at 0°-5° and aluminium chloride (1.04g; 0.011 mole) was added. The mixture was stirred at room temperature for 30 minutes, ice was added slowly and the organic fraction was separated. The aqueous fraction was extracted with chloroform and the combined organic fractions were washed with water, dried (magnesium sulphate) and evaporated. The resulting oil was purified by column chromatography on silica using 9:1 petroleum ether: ethyl acetate as eluent to yield a yellow solid which was recrystallised from petroleum ether to yield pure 4-benzoylbutyrylferrocene mp 96° (3%).

Workup

  1. additionice was added slowly
  2. customthe organic fraction was separated
  3. extractionThe aqueous fraction was extracted with chloroform
  4. washthe combined organic fractions were washed with water
  5. dry with materialdried (magnesium sulphate)
  6. customevaporated
  7. customThe resulting oil was purified by column chromatography on silica using 9:1 petroleum ether
  8. customethyl acetate as eluent to yield a yellow solid which
  9. customwas recrystallised from petroleum ether

Sources & evidence

ORD record
ord-7a7095bb33144f2baccccc0227bdd04d
Source dataset
uspto-grants-1976_06
Patent number
US03966783

Reaction notes

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