Sodium Iodide → Cyclopentane, (2-iodoethoxy)-

HRID 1058753Notes

Reaction equation

HRID 1058753 reaction equation
BrC1C=CC(S(O[CH2:12][CH2:13][O:14][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)(=O)=O)=CC=1.[I-:20].[Na+]>CC(C)=O>[I:20][CH2:12][CH2:13][O:14][CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 18669129HCID 18669129, compound

Product 1

HCID 18669143Cyclopentane, (2-iodoethoxy)-Yield 37%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 2-(cyclopentyloxy)ethyl 4-bromobenzenesulfonate (Preparation 16, 60 mg, 0.17 mmol) in acetone (5 mL) at room temperature was added sodium iodide (200 mg, 1.3 mmol). The mixture was,heated at 35° C. for 16 hours and then cooled. The residual precipitate was removed by filtration and the filtrate was concentrated in vacuo. The residue was partitioned between diethyl ether (10 mL) and water (10 mL). The two layers were separated and the organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to give the title compound (15 mg, 37%) as a brown oil.

Workup

  1. temperaturecooled
  2. customThe residual precipitate was removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was partitioned between diethyl ether (10 mL) and water (10 mL)
  5. customThe two layers were separated
  6. dry with materialthe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8b9601cdb4ce4404aeaccbdbe6e906e4
Source dataset
uspto-grants-2003_02
Patent number
US06518282B1

Reaction notes

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