Pyridine → HCID 67314002, compound

HRID 1391495Notes

Reaction equation

HRID 1391495 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[C:9]=2[CH:21](C2C=NC=CC=2)[OH:22])[CH:5]=[CH:6][CH:7]=1.C(O[C:33](=[O:35])[CH3:34])(=O)C.[N:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[C:9]=2[CH2:21][O:22][C:33](=[O:35])[CH2:34][C:38]2[CH:37]=[N:36][CH:41]=[CH:40][CH:39]=2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 11647674HCID 11647674, compound

Product 1

HCID 67314002HCID 67314002, compound

Procedure

To a solution of 43 mg (0.10 mmol) of 5-(3-chlorophenyl)-3-(2,4-dichlorophenyl)-4-[(3-pyridyl)hydroxymethyl]isoxazole in 2 mL of pyridine was added 19 μL (0.20 mmol) of acetic anhydride. The reaction was stirred overnight at room temperature, and then the pyridine was removed under vacuum. The residue was taken up in ethyl acetate, washed with saturated sodium chloride, and the ethyl acetate fraction dried over magnesium sulfate. The drying agent was filtered off, and the ethyl acetate was removed by rotoevaporation. The crude product was purified by preparative thin layer chromatography (prep TLC) to give 35 mg (0.074 mmol) of 5-(3-chlorophenyl)-3-(2,4-dichlorophenyl)-4-[(3-pyridyl)acetoxymethyl]isoxazole.

Workup

  1. customthe pyridine was removed under vacuum
  2. washwashed with saturated sodium chloride
  3. dry with materialthe ethyl acetate fraction dried over magnesium sulfate
  4. filtrationThe drying agent was filtered off
  5. customthe ethyl acetate was removed by rotoevaporation
  6. customThe crude product was purified by preparative thin layer chromatography (prep TLC)

Sources & evidence

ORD record
ord-9ec8c78fefc341e3a6aafe9c759ae142
Source dataset
uspto-grants-2008_03
Patent number
US07338967B2

Reaction notes

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