Tetraethylene Glycol → 3,6,9,12-Tetraoxapentadec-14-en-1-ol

HRID 1714708Notes

Reaction equation

HRID 1714708 reaction equation
[CH3:1][C:2](C)([O-])[CH3:3].[K+].[CH2:7]([OH:19])[CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][OH:18].C(I)C=C>C1COCC1>[CH2:1]=[CH:2][CH2:3][O:18][CH2:17][CH2:16][O:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][OH:19]

Participants

5

Reactant 3

HCID 8200Tetraethylene GlycolHCID 11166Allyl iodideHCID 23665647Potassium tert-butoxide

Product 1

HCID 101252143,6,9,12-Tetraoxapentadec-14-en-1-olYield 52.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.3 g (19.5 mmol) Potassium tert-butoxide is dissolved in 500 mL dry THF, and 7.18 g (37 mmol) tetraethylene glycol is added dropwise. After stirring for 30 min, a solution of 3.31 g (19.7 mmol) allyl iodide in 60 mL dry THF is added over 1 h, and stirring is continued for 24 h. The crude mixture is filtered over silica gel and the solvent removed in vacuo. The product is purified by silica gel chromatography (gradient: petrol ether/ethyl acetate 10:1→ethyl acetate), yielding 2.41 g 22 (10.3 mmol, 27%) as a colorless liquid.

Workup

  1. stirringstirring
  2. waitis continued for 24 h
  3. filtrationThe crude mixture is filtered over silica gel
  4. customthe solvent removed in vacuo
  5. customThe product is purified by silica gel chromatography (gradient: petrol ether/ethyl acetate 10:1→ethyl acetate)

Sources & evidence

ORD record
ord-e0f110144a264c6e9497951f11dd5afa
Source dataset
uspto-grants-2010_09
Patent number
US07799524B2

Reaction notes

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