Ethylene Glycol → HCID 59030552, compound

HRID 1619195Notes

Reaction equation

HRID 1619195 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][C:5]([C:10]2[N:15]=[CH:14][CH:13]=[CH:12][N:11]=2)([C:8]#[N:9])[CH2:4][CH2:3]1.[CH2:16](O)[CH2:17][OH:18].O>C1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[N:15]1[CH:14]=[CH:13][CH:12]=[N:11][C:10]=1[C:5]1([C:8]#[N:9])[CH2:6][CH2:7][C:2]2([O:18][CH2:17][CH2:16][O:1]2)[CH2:3][CH2:4]1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 962WaterHCID 59030592HCID 59030592, compound

Product 1

HCID 59030552HCID 59030552, compoundYield 80.1%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 241BenzeneSolvent

Procedure

A solution of 4-oxo-1-(pyrimidin-2-yl)cyclohexanecarbonitrile (333 mg, 1.66 mmol), ethylene glycol (96.9 μl, 1.74 mmol), and p-toluenesulfonic acid monohydrate (15.7 mg, 82.7 μmol) in benzene (10 mL) was refluxed for 1.5 h while the water formed during the reaction was removed azeotropically using a Dean-Stark apparatus. After being cooled down to room temperature, the reaction was diluted (Et2O) and washed (2×H2O, 2×sat aqueous NaHCO3, and 2× brine). The organic layer was dried (Na2SO4) and concentrated under reduced pressure. Purification of the residue by flash chromatography (SiO2, 40-50% EtOAc/Hexanes, gradient elution) gave 8-pyrimidin-2-yl-1,4-dioxa-spiro[4,5]decane-8-carbonitrile (325 mg, 1.33 mmol, 80%) as a white solid.

Workup

  1. customformed during the reaction
  2. customwas removed azeotropically
  3. additionthe reaction was diluted (Et2O)
  4. washwashed (2×H2O, 2×sat aqueous NaHCO3, and 2× brine)
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customPurification of the residue
  8. washby flash chromatography (SiO2, 40-50% EtOAc/Hexanes, gradient elution)

Sources & evidence

ORD record
ord-e5bc089b76c94f55a076017268fa652f
Source dataset
uspto-grants-2014_07
Patent number
US08772296B2

Reaction notes

Loading…