Glycol monoethyl ether → HCID 178447880, compound

HRID 1788644Notes

Reaction equation

HRID 1788644 reaction equation
C(OCCO)C.[CH2:7]([C@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[C:18](Cl)[N:17]=2)[CH2:12][CH2:11]1)[CH2:8][CH3:9]>[Zn].O>[CH2:7]([C@H:10]1[CH2:11][CH2:12][C@H:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][N:17]=2)[CH2:14][CH2:15]1)[CH2:8][CH3:9]

Participants

5

Reactant 2

HCID 8076Glycol monoethyl etherHCID 178447879HCID 178447879, compound

Product 1

HCID 178447880HCID 178447880, compoundYield 33.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 962WaterSolvent

Procedure

2-Ethoxyethanol (200 ml), water (40 ml) and zinc powder (20 g) were added to 2-(trans-4-n-propylcyclohexyl)-5-cyano-6-chloropyridine (17.0 g) of Example 6, followed by heating the mixture under reflux for 28 hours, cooling, thereafter filtering, adding toluene (200 ml) and water (500 ml) to the filtrate, stirring, still standing, separating the toluene layer, twice washing it with water, and carrying out the same procedure as in Example 11 to obtain the objective 2-(trans-4- n-propylcyclohexyl)-5-cyanopyridine (5 g). C-N point: 47.6° C. N-I point: 51.9° C.

Workup

  1. temperatureby heating the mixture
  2. temperatureunder reflux for 28 hours
  3. temperaturecooling
  4. filtrationfiltering
  5. additionadding toluene (200 ml) and water (500 ml) to the filtrate
  6. customseparating the toluene layer
  7. washtwice washing it with water

Sources & evidence

ORD record
ord-99a00e326a5c4ebba98eaae64e5e9821
Source dataset
uspto-grants-1987_08
Patent number
US04684477

Reaction notes

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