Potassium Iodide → 3-[5-(4-Cyanophenoxy)pentyl]-5-methylisoxazole

HRID 359802Notes

Reaction equation

HRID 359802 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:20]=[C:19]([CH3:21])[O:18][N:17]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:20]=[C:19]([CH3:21])[O:18][N:17]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 133169783-(5-Bromopentyl)-5-methylisoxazole

Product 1

HCID 133169653-[5-(4-Cyanophenoxy)pentyl]-5-methylisoxazoleYield 53.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5.1 g of 4-cyanophenol, 10 g of 3-(5-bromopentyl)-5-methylisoxazole, 8 g of potassium carbonate, 1 g of potassium iodide and 75 ml of acetonitrile was heated at reflux for 24 hours. The product was isolated and distilled, first at 115°-200° C. (0.1 mm) and then at 160°-190° C. (0.05 mm) to yield a yellow oil which crystallized upon cooling. Recrystallization from hexane-ether afforded 6.2 g of 3-[5-(4-cyanophenoxy)pentyl]-5-methylisoxazole, m.p. 61°-62° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. customThe product was isolated
  4. distillationdistilled, first at 115°-200° C. (0.1 mm)
  5. customat 160°-190° C. (0.05 mm) to yield a yellow oil which
  6. customcrystallized
  7. temperatureupon cooling
  8. customRecrystallization from hexane-ether

Sources & evidence

ORD record
ord-c606db09457f4052b14bc355e1e4dc53
Source dataset
uspto-grants-1991_03
Patent number
US05002960

Reaction notes

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