Acetic Acid → HCID 89488364, compound

HRID 570131

Reaction equation

HRID 570131 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([O:13][CH2:14][C:15]([CH3:17])=O)[NH:10][N:9]=2)=[CH:4][CH:3]=1.C(O)(=O)C.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]3[O:13][CH:14]=[C:15]([CH3:17])[N:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 6101p-Toluenesulfonic acidHCID 178468630HCID 178468630, compound

Product 1

HCID 89488364HCID 89488364, compoundYield 46.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

To a stirred solution of 1-{[3-(4-fluorophenyl)-1H-pyrazol-5-yl]oxy}acetone (0.25 g, 1.0 mmol) in toluene, equipped with dean stark apparatus, acetic acid (2 ml) and p-TsOH (25 mg, cat.) was charged at RT and the reaction mass was refluxed at 130° C. for 16 h. After completion, the reaction was diluted with EtOAc (50 ml) and washed with brine. The organic layer dried over sodium sulphate and concentrated under reduced pressure to get the crude which was then purified by column chromatography 100-200 mesh) eluted with 5-10% ethyl acetate in hexane as eluent to get compound 6-(4-fluorophenyl)-3-methylpyrazolo[5,1-b][1,3]oxazole (0.1 g, yield 43%).

Workup

  1. additionwas charged at RT
  2. washwashed with brine
  3. dry with materialThe organic layer dried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customto get the crude which
  6. customwas then purified by column chromatography 100-200 mesh)
  7. washeluted with 5-10% ethyl acetate in hexane as eluent

Sources & evidence

ORD record
ord-3c0b78a0836c4cfebba1d3ef6e030625
Source dataset
uspto-grants-2015_05
Patent number
US09023844B2

Linked notes

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