Bis(eta-cyclopentadienyl) iron → HCID 178467786, compound

HRID 1658899Notes

Reaction equation

HRID 1658899 reaction equation
[CH-:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH-:6]1[CH:10]=[CH:9][CH:8]=[CH:7]1.[Fe+2:11].ClCCCl.C(=O)=O.[O:19]=[C:20]([CH3:28])[CH2:21][CH2:22][CH2:23][CH2:24][C:25](Cl)=[O:26].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCl>[O:19]=[C:20]([CH3:28])[CH2:21][CH2:22][CH2:23][CH2:24][C:25]([C-:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1)=[O:26].[CH-:6]1[CH:10]=[CH:9][CH:8]=[CH:7]1.[Fe+2:11]

Participants

6

Reactant 4

HCID 7611Bis(eta-cyclopentadienyl) ironHCID 6451240Aluminum(III) ChlorideHCID 13170170HCID 13170170, compoundHCID 131710370HCID 131710370, compound

Product 1

HCID 178467786HCID 178467786, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ferrocene (26g; 0.14 mole) was dissolved in dichloromethane (500 ml) and stirred at -35° (1,2-dichloroethane/dry ice bath). 6-Oxo-heptanoyl chloride from step (a) was added followed by aluminium chloride (18.7g; 0.14 moles) over 30 minutes. Stirring at -35° was continued for another 2 hours and the mixture was poured into ice/water (1 kg). The dichloromethane layer was separated, washed with water (3 × 600 ml), dried over sodium sulphate and concentrated under vacuum, giving a red oil. The desired product was isolated by column chromatography using 9:1 toluene:ethyl acetate as eluent on silica. Recrystallisation of the orange solid from petroleum ether (bp 60-80) afforded the pure compound (3.2g; 73%) mp 70°-71°.

Workup

  1. customThe dichloromethane layer was separated
  2. washwashed with water (3 × 600 ml)
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under vacuum
  5. customgiving a red oil

Sources & evidence

ORD record
ord-3dc5a0073cc4447c817ce25ed1f14440
Source dataset
uspto-grants-1976_06
Patent number
US03966783

Reaction notes

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