Ethylene Glycol → 1,4,7-Trioxaspiro[4.4]nonane

HRID 1365730Notes

Reaction equation

HRID 1365730 reaction equation
[OH:1][C:2]1C(=O)N2C(C3(CCCC3)OCC2)=N[C:3]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18].[CH2:22](O)CO>C1C=CC=CC=1.CCOCC.CC1C=CC(S(O)(=O)=O)=CC=1.O>[O:18]1[C:17]2([CH2:3][CH2:2][O:1][CH2:22]2)[O:19][CH2:20][CH2:21]1

Participants

6

Reactant 2

HCID 174Ethylene GlycolHCID 58962289HCID 58962289, compound

Product 1

HCID 574264341,4,7-Trioxaspiro[4.4]nonaneYield 80.1%

Reagents, catalysts & solvents 3

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of ethyl 3′-hydroxy-4′-oxo-6′,7′-dihydro-4′H-spiro[cyclopentane-1,9′-pyrimido[2,1-c][1,4]oxazine]-2′-carboxylate (15.79 g, 183.5 mmol), ethylene glycol (16.7 mL, 300 mmol) and cat. TsOH.H2O (100 mg) in benzene (100 mL) was heated at reflux using Dean-Stark trap. After 17 h, the reaction mixture was cooled, diluted with ether (150 mL), washed with sat. Na2CO3 and brine (50 mL each), dried (Na2SO4), filtered and concentrated to give yellow liquid. Distillation under reduced pressure afforded the title compound as a yellow liquid (19.13 g, 80%). 1H NMR (500 MHz, CDCl3) δ: 3.9.4 (2H, t, J=7.0 Hz), 3.94-3.90 (4H, m), 3.68 (2H, s), 2.09 (2H, t, J=7.0 Hz).

Workup

  1. temperatureat reflux
  2. temperaturethe reaction mixture was cooled
  3. washwashed with sat. Na2CO3 and brine (50 mL each)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give yellow liquid
  8. distillationDistillation under reduced pressure

Sources & evidence

ORD record
ord-350234b86c124db59950bb75eeae6377
Source dataset
uspto-grants-2011_02
Patent number
US07893055B2

Reaction notes

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