Hydrochloric Acid → 3-(5-Benzyloxypentyl)-7-oxo-cis-bicyclo[3,3,0]oct-2-ene

HRID 1654243Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1654243
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1[CH2:21][C@@H:20]2[C@@H:16]([CH2:17][C:18]3(OCC[O:22]3)[CH2:19]2)[CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(=O)(O)[O-].[Na+]>CC(C)=O.O>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]1[CH2:21][C@@H:20]2[C@@H:16]([CH2:17][C:18](=[O:22])[CH2:19]2)[CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 228526733-(5-Benzyloxypentyl)-7,7-ethylenedioxy-cis-bicyclo-[3,3,0]oct-2-ene

Produkt 1

HCID 228526743-(5-Benzyloxypentyl)-7-oxo-cis-bicyclo[3,3,0]oct-2-eneAusbeute 103,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

6.65 g of 3-(5-benzyloxypentyl)-7,7-ethylenedioxy-cis-bicyclo[3,3,0]oct-2-ene (prepared as described in Preparation 4 or 10) were added to a mixture of 120 ml of acetone, 45 ml of water and 1.0 ml of concentrated hydrochloric acid, and the mixture was stirred for 2 hours at room temperature. After completion of the reaction, sodium bicarbonate was added to the reaction mixture for neutralization, and acetone was distilled off under reduced pressure. A saturated aqueous solution of sodium chloride was added to the residue, and then the mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The solvent was distilled off from the extract under reduced pressure, giving 6.00 g of residue. On purifying this residues by silica gel column chromatography, 5.33 g of the title compound were obtained from the fractions eluted with hexane containing 7-10% by volume of ethyl acetate.

Aufarbeitung

  1. distillationwas distilled off under reduced pressure
  2. additionA saturated aqueous solution of sodium chloride was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off from the
  7. extractionextract under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-89d3986730cc4493bcd051dd1635e5b3
Quelldatensatz
uspto-grants-1995_04
Patentnummer
US05405870

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