Perfluoropropyl iodide → HCID 178448065, compound

HRID 1614117Notes

Reaction equation

HRID 1614117 reaction equation
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([CH:10]2[CH2:15][CH2:14][CH:13]=[CH:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[F:16][C:17]([F:26])([C:22]([F:25])([F:24])[F:23])[C:18](I)([F:20])[F:19]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCCCCC>[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C@H:10]2[CH2:15][CH2:14][C@H:13]([C:18]([F:20])([F:19])[C:17]([F:26])([F:16])[C:22]([F:25])([F:24])[F:23])[CH2:12][CH2:11]2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 33977Perfluoropropyl iodideHCID 178447857HCID 178447857, compound

Product 1

HCID 178448065HCID 178448065, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8058HexaneSolvent

Procedure

A mixture of 0.1 mol of 4-(trans-4-propylcyclohexyl)-cyclohex-1-ene, 0.1 mol of heptafluoropropyl iodide, 10 mol % of tetrakis-(triphenylphosphine)-palladium and 200 ml of hexane is heated under reflux for 24 hours (compare T. Ishihara, Chemistry Letters (1986) 1895). The isomer mixture of the addition product thus formed is, after the catalyst has been filtered off, first heated with tributyl-tin hydride for 90 hours in toluene and reduced. The all-trans product, trans-4-(trans-4-propylcyclohexyl)-1-heptafluoropropylcyclohexane, is finally obtained by separating the thiourea inclusion compound from a solution in methanol.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 24 hours (compare T. Ishihara, Chemistry Letters (1986) 1895)
  3. additionThe isomer mixture of the addition product
  4. customthus formed
  5. filtrationafter the catalyst has been filtered off
  6. temperaturefirst heated with tributyl-tin hydride for 90 hours in toluene

Sources & evidence

ORD record
ord-66db2f99b61547f9a400e2559cab4e07
Source dataset
uspto-grants-1993_03
Patent number
US05196140

Reaction notes

Loading…