Potassium Carbonate → 3-Methyl-5-{5-[4-(5-oxazolyl)phenoxy]pentyl}isoxazole

HRID 2165423Notes

Reaction equation

HRID 2165423 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=2)[O:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].S([CH2:37][N+:38]#[C-:39])(C1C=CC(C)=CC=1)(=O)=O>CO>[CH3:1][C:2]1[CH:6]=[C:5]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[CH:15][C:16]([C:17]3[O:18][CH:39]=[N:38][CH:37]=3)=[CH:19][CH:20]=2)[O:4][N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 161915Tosylmethyl isocyanideHCID 64834254-[5-(3-Methyl-5-isoxazolyl)pentyloxy]benzaldehyde

Product 1

HCID 200639913-Methyl-5-{5-[4-(5-oxazolyl)phenoxy]pentyl}isoxazoleYield 48%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 10.00 g of 4-[5-(3-methyl-5-isoxazolyl)pentyloxy]benzaldehyde, 10.0 g of potassium carbonate and 7.14 g of tosylmethyl isocyanide (4-CH3C6H4 -SO2CH2NC) in 90 ml of methanol was heated at reflux for 3 hours. The reaction mixture was concentrated in vacuo, and the residue was extracted with methylene dichloride. The extract was washed with water, the product isolated and recrystallized from isopropyl acetate-hexane. Further purification by flash filtration through a silica gel pad, eluting with isopropyl acetate, and recrystallization from isopropyl acetate-hexane gave 5.43 g (48%) of 3-methyl-5-{5-[4-(5-oxazolyl)phenoxy]pentyl}isoxazole, yellow powder, m.p. 91°-93° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. extractionthe residue was extracted with methylene dichloride
  5. washThe extract was washed with water
  6. customthe product isolated
  7. customrecrystallized from isopropyl acetate-hexane
  8. customFurther purification
  9. filtrationby flash filtration through a silica gel pad
  10. washeluting with isopropyl acetate, and recrystallization from isopropyl acetate-hexane

Sources & evidence

ORD record
ord-4b806522799a4ad197a47354514c462d
Source dataset
uspto-grants-1990_07
Patent number
US04939267

Reaction notes

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