Diethyl Ether → 12079-65-1

HRID 1494663Notes

Reaction equation

HRID 1494663 reaction equation
[C:1]([O-])(=[O:3])C.[Mn+2:5].[C:6]([O-])(=[O:8])C.[CH:10]1[CH2:14][CH:13]=[CH:12][CH:11]=1.C[CH2:16][O:17]CC>CCCCC>[C-:1]#[O+:3].[C-:6]#[O+:8].[C-:16]#[O+:17].[CH-:10]1[CH:14]=[CH:13][CH:12]=[CH:11]1.[Mn:5]

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 7612CyclopentadieneHCID 12525Manganous Acetate

Product 1

HCID 6155112079-65-1Yield 54%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Conditions

Temperature
-78 °C

Procedure

A 300 ml stainless steel autoclave was charged with 2.00 g manganese (II) acetate (11.6 mmol), 3.07 g cyclopentadiene monomer (46.5 mmol), 70 ml ether, and 4.0 g TEA (35.1 mmol) pre-mixed with some of the ether. The autoclave was sealed and purged with CO. The carbonylation was carried out at 550 psi total pressure and a temperature of 175° C. for two hours. The cooled reactor was vented and the contents transferred to an Erlenmeyer flask. A solution of 10% HCl was added carefully until the salts dissolved. The organic layer was separated and washed with water, dried (MgSO4), filtered and evaporated leaving a red oil. Pentane (100 ml) was added. Cooling to -78° C. for several hours gave 1.10 g (54%) of cyclopentadienylmanganese tricarbonyl product as yellow crystals, mp 65°-69° C.

Workup

  1. customThe autoclave was sealed
  2. custompurged with CO
  3. additionA solution of 10% HCl was added carefully until the salts
  4. dissolutiondissolved
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customleaving a red oil

Sources & evidence

ORD record
ord-850106dea43e40e5a904dd9723bd50a1
Source dataset
uspto-grants-1991_06
Patent number
US05026885

Reaction notes

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