Isopropanol → HCID 13105450, compound

HRID 1462412Notes

Reaction equation

HRID 1462412 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([C:17]3[CH:21]=[CH:20][S:19][CH:18]=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>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([C:17]3[CH:21]=[CH:20][S:19][CH:18]=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 30697874-Oxazoleacetic acid, 2-(p-fluorophenyl)-5-(3-thienyl)-

Product 1

HCID 13105450HCID 13105450, compoundYield 74.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

One g of 2-[2-(4-fluorophenyl)-5-(3-thienyl)-4-oxazolyl]acetic acid, 0.93 g of 2-chloro-1-methyl-pyridinium iodide and 0.2 g of isopropanol are dissolved in 40 ml of tetrahydrofuran, and 0.66 g of triethylamine is added dropwise thereto. The mixture is stirred at room temperature for 18 hours. Then, water is added to the reaction mixture, and said mixture is condensed 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. Said extract is dried and then condensed to remove solvent, and the residue is recrystallized from ethanol. 0.85 g of isopropyl 2-[2-(4-fluorophenyl)-5-(3-thienyl)-4-oxazolyl]acetate is thereby obtained.

Workup

  1. customcondensed 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. extractionSaid extract
  6. customis dried
  7. customcondensed
  8. customto remove solvent
  9. customthe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-fb26021f20794cbb8ec90f3950573763
Source dataset
uspto-grants-1984_07
Patent number
US04460596

Reaction notes

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