Potassium Iodide → HCID 86650279, compound

HRID 1889218Notes

Reaction equation

HRID 1889218 reaction equation
[CH2:1]([OH:19])[CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][OH:18].[S:20](Cl)([C:23]1[CH:29]=[CH:28][C:26](C)=[CH:25][CH:24]=1)(=[O:22])=[O:21].[I-].[K+]>C(Cl)Cl.[Ag]=O>[OH:18][CH2:17][CH2:16][O:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][O:3][CH2:2][CH2:1][O:19][S:20]([C:23]1[CH:29]=[CH:28][CH:26]=[CH:25][CH:24]=1)(=[O:22])=[O:21]

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 73974-Toluenesulfonyl chlorideHCID 17472Hexaethylene Glycol

Product 1

HCID 86650279HCID 86650279, compoundYield 89.7%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6344DichloromethaneSolvent

Procedure

Hexaethyleneglycol (11) (2.82 g, 10 mmol, 1 equiv.) was dissolved in CH2Cl2 (100 mL) under a N2 atmosphere, and silver oxide (3.48 g, 15 mmol, 1.5 equiv.) added followed by tosyl chloride (2.10 g, 11 mmol, 1.1 equiv.) and potassium iodide (332 mg, 2 mmol, 0.2 mmol). The solution was stirred at rt for 1 h then concentrated and filtered through celite eluting with ethyl acetate. The filtrate was concentrated in vacuo to give a pale yellow oil which was purified by column chromatography on silica (ethyl acetate) to give 12 (3.79 g, 87%) as a pale yellow oil.

Workup

  1. concentrationthen concentrated
  2. filtrationfiltered through celite
  3. washeluting with ethyl acetate
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto give a pale yellow oil which
  6. customwas purified by column chromatography on silica (ethyl acetate)

Sources & evidence

ORD record
ord-3a24443e998749d881d551c55d86c7c3
Source dataset
uspto-grants-2013_08
Patent number
US08501991B2

Reaction notes

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