Isopropanol → HCID 13392293, compound

HRID 235885Notes

Reaction equation

HRID 235885 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([C:17]3[O:18][CH:19]=[CH:20][CH:21]=3)=[C:11]([CH2:13][C:14]([OH:16])=[O:15])[N:12]=2)=[CH:4][CH:3]=1.[I-].ClC1C=[CH:28][CH:27]=[CH:26][N+]=1C.C(O)(C)C.C(N(CC)CC)C>O1CCCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([C:17]3[O:18][CH:19]=[CH:20][CH:21]=3)=[C:11]([CH2:13][C:14]([O:16][CH:27]([CH3:28])[CH3:26])=[O:15])[N:12]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 13392284HCID 13392284, compound

Product 1

HCID 13392293HCID 13392293, compoundYield 43.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.0 g of 2-[2-(4-chlorophenyl)-5-(2-furyl)-4-oxazolyl]acetic acid, 1.0 g of 2-chloro-1-methylpyridinium iodide and 0.24 g of isopropanol are dissolved in 30 ml of tetrahydrofuran, and 0.8 g of triethylamine is added dropwise thereto. The mixture is stirred at room temperature for 10 hours. Water is added to the mixture, and the aqueous mixture is evaporated under reduced pressure to remove tetrahydrofuran. The residue is extracted with ethyl acetate, and the extract is washed with an aqueous 20% citric acid solution, an aqueous sodium bicarbonate solution and water, successively. Then, the extract is dried and then evaporated under reduced pressure to remove solvent. The residue is recrystallized from ethanol, whereby 0.5 g of isopropyl 2-[2-(4-chlorophenyl)-5-(2-furyl)-4-oxazolyl]acetate is obtained. Yield: 43.6%

Workup

  1. customthe aqueous mixture is evaporated under reduced pressure
  2. customto remove tetrahydrofuran
  3. extractionThe residue is extracted with ethyl acetate
  4. washthe extract is washed with an aqueous 20% citric acid solution
  5. customThen, the extract is dried
  6. customevaporated under reduced pressure
  7. customto remove solvent
  8. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-76fc84c1223b43ebbc7e590e5b53cea3
Source dataset
uspto-grants-1987_02
Patent number
US04642313

Reaction notes

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