Hydrochloric Acid → HCID 56609317, compound

HRID 1789611Notes

Reaction equation

HRID 1789611 reaction equation
[CH2:1]([CH:9]1[C:13](=[CH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])[C:12](=[O:24])[CH:11]=[CH:10]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C1([Se][Cl:32])C=CC=CC=1.[H][H].Cl>ClCCl.O.N1C=CC=CC=1>[Cl:32][C:11]1[C:12](=[O:24])[C:13](=[CH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH:10]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 21928Chloroselenobenzene2×HCID 56635890HCID 56635890, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 56609317HCID 56609317, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolvent3×HCID 6344DichloromethaneSolvent

Procedure

17 mg (51 mmol) of 4-octyl-5-(6-methoxycarbonylhexylidene)-2-cyclopentenone was dissolved in 1 ml of dichloromethane and 23 μl (280 μmol) of pyridine was added thereto. With stirring, 49 mg (254 mmol) of phenyl selenium chloride was added to the mixture and the reaction mixture was refluxed. 10 hours later, 23 μl (280 mmol) of pyridine and 49 mg (254 mmol) of phenyl selenium chloride were further added and the mixture was refluxed for 25 hours. 0.5 ml of pyridine was added to the reaction mixture and then, with vigorous stirring, 35% aqueous hydrogen, peroxide was further added and the mixture was stirred for another 1 hour. Hydrochloric acid and water were added thereto for extraction and the aqueous layer was then extracted twice with dichloromethane. The organic layer was washed first with a saturated aqueous solution of sodium hydrogencarbonate and then with a saturated saline solution and dried over sodium sulfate anhydride. Thereafter, it was filtrated, concentrated, and chromatographed on a column of silica gel (silica gel 5 g; eluent, hexane:ethyl acetate=30:1→10:1) to obtain 10 mg (yield 53%) of 2-chloro-4-octyl-5-(6-methoxycarbonylhexylidene)-2-cyclopentenone.

Workup

  1. temperaturethe reaction mixture was refluxed
  2. temperaturethe mixture was refluxed for 25 hours
  3. stirringthe mixture was stirred for another 1 hour
  4. extractionfor extraction
  5. extractionthe aqueous layer was then extracted twice with dichloromethane
  6. washThe organic layer was washed first with a saturated aqueous solution of sodium hydrogencarbonate
  7. dry with materialwith a saturated saline solution and dried over sodium sulfate anhydride
  8. filtrationThereafter, it was filtrated
  9. concentrationconcentrated
  10. customchromatographed on a column of silica gel (silica gel 5 g; eluent, hexane:ethyl acetate=30:1→10:1)

Sources & evidence

ORD record
ord-e533bfae54e94f988bfce1aa6ba01c96
Source dataset
uspto-grants-1987_08
Patent number
US04689426

Reaction notes

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