HCID 129792804, compound → HCID 178520603, compound

HRID 917865Notes

Reaction equation

HRID 917865 reaction equation
[C-:1]1([C:6]2([CH2:11][CH2:12][CH2:13][OH:14])[CH2:10][CH2:9][CH2:8][O:7]2)[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH-:15]1[CH:19]=[CH:18][CH:17]=[CH:16]1.[Fe+2:20]>FC(F)(F)C(O)=O>[C-:1]1([C:6]([C-:15]2[CH:19]=[CH:18][CH:17]=[CH:16]2)([CH2:11][CH2:12][CH2:13][OH:14])[CH2:10][CH2:9][CH2:8][OH:7])[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH-:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[Fe+2:20].[CH-:1]1[CH:5]=[CH:4][CH:3]=[CH:2]1.[Fe+2:20]

Participants

3

Reactant 1

HCID 129792804HCID 129792804, compound

Product 1

HCID 178520603HCID 178520603, compoundYield 207.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
25 °C

Procedure

One gram of 2-ferrocenyl-2-(3-hydroxypropyl)tetrahydrofuran (II) was dissloved in 10 ml of trifluoroacetic acid at 25°C for 2 hours. The trifluoroacetic acid was removed under reduced pressure at 25°C and ferrocene, 5.41 g (0.032 mole), dissolved in 25 ml of methylene chloride, was added to the residue. The solution was stirred 40 hours at 25°C and then treated with 50 ml of H2O and enough ascorbic acid solution (drop by drop) to reduce the ferricinium ion present. The phases were separated and the aqueous phase was extracted with 25 ml of methylene chloride. The methylene chloride phases were combined and dried over calcium chloride. The solvent (CH2Cl2) was removed under reduced pressure and the residue was heated at 175°/0.25 mm pressure of 15 minutes to remove residual unreacted ferrocene. The nonvolatile residue was then dissolved in a 2% methyl alcohol in ethyl acetate solution and chromatographed on a dry 3.6 cm by 25 cm alumina column. Extraction of the major yellow band with methyl alcohol gave 1.1 g (69% yield) of 4,4-diferrocenylheptane-1,7-diol (IV). Recrystallization from benzene gave a mp of 168°-171°C. An additional recrystallization from methyl alcohol gave a mp of 169°-171°C.

Workup

  1. customThe trifluoroacetic acid was removed under reduced pressure at 25°C
  2. dissolutionferrocene, 5.41 g (0.032 mole), dissolved in 25 ml of methylene chloride
  3. additionwas added to the residue
  4. additiontreated with 50 ml of H2O and enough ascorbic acid solution (drop by drop)
  5. customThe phases were separated
  6. extractionthe aqueous phase was extracted with 25 ml of methylene chloride
  7. dry with materialdried over calcium chloride
  8. customThe solvent (CH2Cl2) was removed under reduced pressure
  9. temperaturethe residue was heated at 175°/0.25 mm pressure of 15 minutes
  10. customto remove residual unreacted ferrocene
  11. dissolutionThe nonvolatile residue was then dissolved in a 2% methyl alcohol in ethyl acetate solution
  12. customchromatographed on a dry 3.6 cm by 25 cm alumina column
  13. extractionExtraction of the major yellow band with methyl alcohol

Sources & evidence

ORD record
ord-096ee955d2bd4e6296c98a51ac938fe8
Source dataset
uspto-grants-1976_07
Patent number
US03968126

Reaction notes

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