Bis(eta-cyclopentadienyl) iron → HCID 178424444, compound

HRID 1658892Notes

Reaction equation

HRID 1658892 reaction equation
[C:1]1([CH3:16])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[CH:9]1[CH2:12][CH2:11][CH:10]1[C:13](Cl)=[O:14].[CH-:17]1[CH:21]=[CH:20][CH:19]=[CH:18]1.[CH-:22]1[CH:26]=[CH:25][CH:24]=[CH:23]1.[Fe+2:27].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[C:1]1([CH3:16])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[CH:9]1[CH2:12][CH2:11][CH:10]1[C:13]([C-:17]1[CH:21]=[CH:20][CH:19]=[CH:18]1)=[O:14].[CH-:22]1[CH:26]=[CH:25][CH:24]=[CH:23]1.[Fe+2:27]

Participants

5

Reactant 3

HCID 7611Bis(eta-cyclopentadienyl) ironHCID 6451240Aluminum(III) ChlorideHCID 54501877HCID 54501877, compound

Product 1

HCID 178424444HCID 178424444, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Mesityl-cyclobutan-2-oic acid chloride (assumed to be 0.1 mole) and ferrocene (18.6g; 0.1 mole) in dry methylene chloride (200 ml) were stirred at 0°-5° and aluminium chloride (20g; 0.15 mole) was added. The mixture was stirred at 0°-5° for 30 minutes and at room temperature for 1 hr; 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 and dried (magnesium sulphate). The solvent was evaporated under reduced pressure to yield a red oil which was purified by column chromatography on silica using 10:1 petroleum ether/ethyl acetate as eluent. The major band gave a red oil which was recrystallised from petroleum ether to give orange crystals of 1-mesityl-2-ferrocenoyl cyclobutane mp 113°-114.5° (20%).

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. customThe solvent was evaporated under reduced pressure
  7. customto yield a red oil which
  8. customwas purified by column chromatography on silica using 10:1 petroleum ether/ethyl acetate as eluent
  9. customThe major band gave a red oil which
  10. customwas recrystallised from petroleum ether

Sources & evidence

ORD record
ord-d1499bcdfb37474a89d441681592f118
Source dataset
uspto-grants-1976_06
Patent number
US03966783

Reaction notes

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