Sodium Iodide → HCID 13151500, compound

HRID 1648861Notes

Reaction equation

HRID 1648861 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][C@H:11]([CH2:13]OS(C3C=CC(C)=CC=3)(=O)=O)[CH2:10][O:9]2)=[CH:4][CH:3]=1.[I-:25].[Na+]>CC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:12][C@H:11]([CH2:13][I:25])[CH2:10][O:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 13151496HCID 13151496, compound

Product 1

HCID 13151500HCID 13151500, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 9.2 g of trans-2-(4-fluorophenyl)-4-(tosyloxymethyl)tetrahydrofuran and 12.6 g of sodium iodide in 130 ml of acetone is heated under reflux for 6 hours. The solvent is then distilled off under reduced pressure, and the residue is extracted with ether. The extract is washed with water and dried over magnesium sulfate, and the solvent is distilled off to give a quantitative yield of trans-2-(4-fluorophenyl)-4-(iodomethyl)tetrahydrofuran as colorless oil, nD27 1.5675.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 6 hours
  3. distillationThe solvent is then distilled off under reduced pressure
  4. extractionthe residue is extracted with ether
  5. washThe extract is washed with water
  6. dry with materialdried over magnesium sulfate
  7. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-8f60bf87c22e45f3a1681feb56001be0
Source dataset
uspto-grants-1983_11
Patent number
US04414216

Reaction notes

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