Potassium Carbonate → p-Ferrocenylphenylacetylene

HRID 2111462Notes

Reaction equation

HRID 2111462 reaction equation
C[Si](C)(C)[C:3]#[C:4][C:5]1[CH:10]=[CH:9][C:8]([C-:11]2[CH:15]=[CH:14][CH:13]=[CH:12]2)=[CH:7][CH:6]=1.[CH-:18]1[CH:22]=[CH:21][CH:20]=[CH:19]1.[Fe+2:23].C([O-])([O-])=O.[K+].[K+]>C1COCC1.CO.CCOCC>[C:4]([C:5]1[CH:10]=[CH:9][C:8]([C-:11]2[CH:15]=[CH:14][CH:13]=[CH:12]2)=[CH:7][CH:6]=1)#[CH:3].[CH-:18]1[CH:22]=[CH:21][CH:20]=[CH:19]1.[Fe+2:23]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 131725739HCID 131725739, compound

Product 1

HCID 12983857p-FerrocenylphenylacetyleneYield 90%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of 3 (1.5 g, 4.2 mmol) in anhydrous THF/MeOH (2:1, 30 mL) was treated with K2CO3 (1.2 g, 8.4 mmol) and the mixture was stirred at rt for 30 min. The solvent was removed under reduced pressure affording an orange solid. The residue was dissolved in ether (50 mL), washed with H2O (3×50 mL), dried (MgSO4) and filtered. The solvent was removed under reduced pressure. Purification by column chromatography (silica, petroleum ether/ethyl ether, 10:2) afforded an orange solid (1.0 g, 90%): mp 104-106° C.; 1H NMR δ 3.11 (s, 1H), 4.04 (s, 5H), 4.35 (t, J=2.4 Hz, 2H), 4.65 (t, J=2.4 Hz, 2H), 7.42 (s, 4H); 13C NMR δ 66.5, 69.3, 69.7, 84.0, 94.1, 105.5, 120.3, 125.7, 132.1, 140.3; FAB-MS obsd 286.0460, calcd exact mass 286.0445 (C18H14Fe). Physical properties concur with published data (Simionescu et al. (1976) J. Organomet. Chem., 113: 23-28).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customaffording an orange solid
  3. washwashed with H2O (3×50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure
  7. customPurification by column chromatography (silica, petroleum ether/ethyl ether, 10:2)

Sources & evidence

ORD record
ord-f40efbad4ecf4c10abf769c6c46c6ee9
Source dataset
uspto-grants-2009_04
Patent number
US07518905B2

Reaction notes

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