Methanol → 3-(2,4-Dichloro-phenyl)-2,6-dimethyl-pyrazolo[5,1-b]oxazol-7-ol

HRID 1671343Notes

Reaction equation

HRID 1671343 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]2[N:17]=[C:16]([CH3:18])[C:15](C=O)=[C:11]2[O:12][C:13]=1[CH3:14].C1C=C(Cl)C=C(C(OO)=[O:29])C=1.C([O-])([O-])=O.[K+].[K+].CO>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]2[N:17]=[C:16]([CH3:18])[C:15]([OH:29])=[C:11]2[O:12][C:13]=1[CH3:14]

Participants

6

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 866389413-(2,4-Dichloro-phenyl)-2,6-dimethyl-pyrazolo[5,1-b]oxazole-7-carbaldehyde

Product 1

HCID 591861133-(2,4-Dichloro-phenyl)-2,6-dimethyl-pyrazolo[5,1-b]oxazol-7-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

3-(2,4-Dichloro-phenyl)-2,6-dimethyl-pyrazolo[5,1-b]oxazole-7-carbaldehyde (750 mg, 2.426 mmol) and m-CPBA (897 mg, 3.64 mmol) are stirred in DCM (10.5 ml) at RT for 3 hours, whereupon the reaction mixture is diluted with DCM (120 ml). The organic phase is washed with sat. NaHCO3 (70 ml) and the phases separated via a phase separator. Back extraction of the aqueous phase with DCM (50 ml) is carried out and the combined organic phases are concentrated in vacuo. The resultant yellow gum is dissolved in MeOH (16.80 ml) and K2CO3 (1676 mg, 12.13 mmol) is added. The reaction is stirred at RT for 30 mins before the MeOH is removed in vacuo. The resulting solid is diluted with water (˜100 ml) and the product is extracted into EtOAc (2×100 ml). The combined organic extracts are washed with brine, dried over MgSO4 and concentrated in vacuo. The crude product is isolated as a light orange solid which is dissolved DCM (15 ml), cooled to 0° C. and the resultant solid collected by filtration to afford the title compound as a pale yellow solid. MS: m/z 297.15 [M+H]+.

Workup

  1. washThe organic phase is washed with sat. NaHCO3 (70 ml)
  2. customthe phases separated via a phase separator
  3. extractionBack extraction of the aqueous phase with DCM (50 ml)
  4. concentrationthe combined organic phases are concentrated in vacuo
  5. dissolutionThe resultant yellow gum is dissolved in MeOH (16.80 ml)
  6. customis removed in vacuo
  7. additionThe resulting solid is diluted with water (˜100 ml)
  8. extractionthe product is extracted into EtOAc (2×100 ml)
  9. washThe combined organic extracts are washed with brine
  10. dry with materialdried over MgSO4
  11. concentrationconcentrated in vacuo
  12. customThe crude product is isolated as a light orange solid which
  13. filtrationthe resultant solid collected by filtration

Sources & evidence

ORD record
ord-bcce42d80ce24e559ce212c009bd4acb
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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