HCID 129792804, compound → HCID 131710381, compound

HRID 917866Notes

Reaction equation

HRID 917866 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]([CH2:10][CH2:9][CH2:8][OH:7])=[CH:11][CH2:12][CH2:13][OH:14])[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH-:15]1[CH:19]=[CH:18][CH:17]=[CH:16]1.[Fe+2:20]

Participants

3

Reactant 1

HCID 129792804HCID 129792804, compound

Product 1

HCID 131710381HCID 131710381, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2-Ferrocenyl-2-(3-hydroxypropyl)tetrahydrofuran (II), 20.5 g (0.065 mole), was dissolved in 100 ml of trifluoroacetic acid at 25°C with external cooling (in an ice bath). After 5 hours about half of the trifluoroacetic acid was removed under reduced pressure at 25°C. The residue was dissolved in 200 ml of tetrahydrofuran (THF). Then 100 ml of 6N NaOH was added with cooling and the mixture was stirred overnight. The THF phase was separated and the THF removed under reduced pressure. The product crystallized out in the form of plates. The plates were suspended in 500 ml of water, filtered and then washed twice on the filter with 50 ml portions of water. The wet cake was removed from the filter, triturated with 50 ml of ether and then filtered to give 11.0 grams of V, mp 85°-88°C. An additional 2.0 g of material, mp 85°-88°C, was recovered from the liquid phases to give a total yield of 4-ferrocenyl-3heptene-1,7-diol of 13.0 g (63% yield).

Workup

  1. temperaturewith external cooling (in an ice bath)
  2. customAfter 5 hours about half of the trifluoroacetic acid was removed under reduced pressure at 25°C
  3. dissolutionThe residue was dissolved in 200 ml of tetrahydrofuran (THF)
  4. additionThen 100 ml of 6N NaOH was added
  5. temperaturewith cooling
  6. customThe THF phase was separated
  7. customthe THF removed under reduced pressure
  8. customThe product crystallized out in the form of plates
  9. filtrationfiltered
  10. washwashed twice on the
  11. filtrationfilter with 50 ml portions of water
  12. customThe wet cake was removed from the filter
  13. customtriturated with 50 ml of ether
  14. filtrationfiltered
  15. customto give 11.0 grams of V, mp 85°-88°C
  16. customAn additional 2.0 g of material, mp 85°-88°C, was recovered from the liquid phases

Sources & evidence

ORD record
ord-5c8f6acd738f43ed9769c88ce2f080ca
Source dataset
uspto-grants-1976_07
Patent number
US03968126

Reaction notes

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