Ethylene Glycol → HCID 57837478, compound

HRID 731750Notes

Reaction equation

HRID 731750 reaction equation
C1(C([C:6]2[C:7]([CH:15]3[CH2:17][CH2:16]3)=[N:8][N:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=23)=O)CC1.C(O)CO>C1C=CC=CC=1>[CH:15]1([C:7]2[CH:6]=[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][N:9]3[N:8]=2)[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 57837444HCID 57837444, compound

Product 1

HCID 57837478HCID 57837478, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Cyclopropyl(2-cyclopropylpyrazolo[1,5-a]pyridin-3-yl)methanone (1.0 g, 4.42 mmol) was heated in benzene (80 ml) to reflux in a Dean-Stark apparatus, in the presence of TsOH monohydrate (0.8 g, 4.21 mmol, 0.95 eq.), for 10 minutes. Freshly distilled ethylene glycol (2.0 g, 32.24 mmol, 7.3 eq.) was added and the biphasic solution maintained at reflux for a further 12 hours. The reaction was cooled to rt and extracted with a saturated NaHCO3 solution (25 ml×3). The organic phase was dried over Na2SO4, filtered and concentrated in-vacuo. Purification by column chromatography (4:1 hexane:ethyl acetate) provided 2-cyclopropylpyrazolo[1,5-a]pyridine as a faintly yellow oil (0.61 g, 3.85 mmol, 87%).

Workup

  1. temperaturethe biphasic solution maintained
  2. temperatureat reflux for a further 12 hours
  3. extractionextracted with a saturated NaHCO3 solution (25 ml×3)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in-vacuo
  7. customPurification by column chromatography (4:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-78220ec772a440c7996985c136e70b2e
Source dataset
uspto-grants-2009_09
Patent number
US07585875B2

Reaction notes

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