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

HRID 1714713Notes

Reaction equation

HRID 1714713 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>[CH2:3]([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])[CH:2]=[CH2:1]

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

To an anhydrous solution of potassium tert-butoxide (2.3 g, 19.5 mmol) in THF (500 mL), tetraethylene glycol (7.18 g, 37.0 mmol) is added at room temperature. The resulting mixture is stirred for 30 min, and a solution of allyl iodide (3.31 g, 19.7 mmol) in dry THF (60 mL) is added dropwise over 1 h. The reaction mixture is stirred for 30 h and filtered through a silica plug (10 g) using ethyl acetate (800 mL) to elute all product. After evaporation of the solvent in vacuo, the product is purified by column chromatography using a solvent gradient petrol ether/ethyl acetate 10:1 to ethyl acetate 100% yielding a colourless oil (2.41 g, 10.3 mmol, 27%).

Workup

  1. stirringThe reaction mixture is stirred for 30 h
  2. filtrationfiltered through a silica plug (10 g)
  3. washto elute all product
  4. customAfter evaporation of the solvent in vacuo
  5. customthe product is purified by column chromatography

Sources & evidence

ORD record
ord-5947f45e52264e4e80a20a2d47b7a8ac
Source dataset
uspto-grants-2010_09
Patent number
US07799524B2

Reaction notes

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