Sodium Chloride → 2-(5-Iodo-pentyloxy)-tetrahydro-pyran

HRID 269423Notes

Reaction equation

HRID 269423 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][O:9]1.[I-:14].[Na+].[Cl-].[Na+]>CC(C)=O>[I:14][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][O:9]1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 5238Sodium IodideHCID 1144672H-Pyran, 2-[(5-chloropentyl)oxy]tetrahydro-

Product 1

HCID 117021222-(5-Iodo-pentyloxy)-tetrahydro-pyranYield 88%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A solution of 2-(5-chloropentyloxy)tetrahydro-2H-pyrane (10) (20.67 g, 0.1 mol) in dry acetone (50 mL) was added in drops to a magnetically stirred solution of sodium iodide (16.49 g, 0.11 mol) in dry acetone (150 mL). The reaction mixture was refluxed in a nitrogen atmosphere over night. After cooling the precipitated sodium chloride was filtered out and acetone was distilled out on a rotary evaporator. The residue which still contained some sodium chloride was dissolved in dry pentane (200 mL). Sodium chloride was filtered out and pentane distilled out on a rotary evaporator, yielding 26.2 g (88%) of a yellowish brown oil. NMR indicated a pure product.

Workup

  1. temperatureThe reaction mixture was refluxed in a nitrogen atmosphere over night
  2. filtrationwas filtered out and acetone
  3. distillationwas distilled out on a rotary evaporator
  4. dissolutionwas dissolved in dry pentane (200 mL)
  5. filtrationSodium chloride was filtered out and pentane
  6. distillationdistilled out on a rotary evaporator

Sources & evidence

ORD record
ord-1085379a749042fcbde73cef40307b71
Source dataset
uspto-grants-2008_11
Patent number
US07446226B2

Reaction notes

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