Selenium Dioxide → HCID 54277598, compound

HRID 225158Notes

Reaction equation

HRID 225158 reaction equation
[C:1]([CH:3]([CH2:7][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:4]([OH:6])=[O:5])#[N:2].[Se](=O)=O>ClC1C=CC=CC=1>[C:1]([C:3](=[CH:7][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:4]([OH:6])=[O:5])#[N:2]

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 23329210HCID 23329210, compound

Product 1

HCID 54277598HCID 54277598, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 11.5 g of 16A, 5.5 g of selenium dioxide and 30 ml of chlorobenzene was refluxed at 135° C. Then the chlorobenzene was distilled off under reduced pressure. The residue was extracted with hot hexane. The hexane was evaporated from the extract under reduced pressure. 30 ml of chlorobenzene was added to the residue and the mixture was refluxed overnight. The chlorobenzene was evaporated under reduced pressure. The residue was extracted with ether. The extract was cooled to give a solid, which was recrystallized from hexane to give the E-isomer of the ethyl ester of 2-cyano-4-oxo-4-phenyl-2-butenoic acid (16B) mp: 74°-75° C.

Workup

  1. distillationThen the chlorobenzene was distilled off under reduced pressure
  2. extractionThe residue was extracted with hot hexane
  3. customThe hexane was evaporated from the
  4. extractionextract under reduced pressure
  5. addition30 ml of chlorobenzene was added to the residue
  6. temperaturethe mixture was refluxed overnight
  7. customThe chlorobenzene was evaporated under reduced pressure
  8. extractionThe residue was extracted with ether
  9. temperatureThe extract was cooled
  10. customto give a solid, which
  11. customwas recrystallized from hexane

Sources & evidence

ORD record
ord-afda572552c5409d993e7dce69a7fd80
Source dataset
uspto-grants-1980_11
Patent number
US04235923

Reaction notes

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