Dimethyl Sulfide → 4-(4-Chlorophenyl)isoxazole-3-carbaldehyde

HRID 1506652Notes

Reaction equation

HRID 1506652 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](/[CH:13]=C/C3C=CC=CC=3)=[N:10][O:11][CH:12]=2)=[CH:4][CH:3]=1.[O:21]=[O+][O-].CSC>C(Cl)Cl.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH:13]=[O:21])=[N:10][O:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 90280212HCID 90280212, compound

Product 1

HCID 902802044-(4-Chlorophenyl)isoxazole-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
-78 °C

Procedure

(E)-4-(4-Chlorophenyl)-3-styrylisoxazole (2 g, 7.1 mmol) was dissolved in DCM/MeOH (20 mL/2 mL) and cooled to −78° C. The reaction was placed under ozonolysis conditions (O3 bubbling) until full disappearance of starting material. DMS (8 mL) was added and the reaction was let warm to ambient temperature. After 15 h, the reaction was partitioned between EtOAc and H2O. The organics were separated, washed with saturated aqueous NaHCO3, and dried with saturated aqueous NaCl. Solvents were removed in vacuo and the residue purified by column chromatography on silica to provide the desired product: MS (m/z) 208.0 [M+H]+.

Workup

  1. temperaturethe reaction was let warm to ambient temperature
  2. customthe reaction was partitioned between EtOAc and H2O
  3. customThe organics were separated
  4. washwashed with saturated aqueous NaHCO3
  5. dry with materialdried with saturated aqueous NaCl
  6. customSolvents were removed in vacuo
  7. customthe residue purified by column chromatography on silica

Sources & evidence

ORD record
ord-4c36f1ce27fc457e8309a2c96e55c168
Source dataset
uspto-grants-2015_12
Patent number
US09220710B2

Reaction notes

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