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Calcium Carbonate → 2-(1-Phenylcyclopentyl)acetaldehyde

HRID 1734905
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1734905
[C:1](=[O:4])([O-])[O-].[Ca+2].[C:6]1([C:12]2([CH2:17]C3SCCCS3)[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(#N)C.O.C(OCC)(=O)C>[C:6]1([C:12]2([CH2:17][CH:1]=[O:4])[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 10112Calcium CarbonateHCID 199661182-(1-Phenylcyclopentyl)methyl-1,3-dithiane

Produkt 1

HCID 199660432-(1-Phenylcyclopentyl)acetaldehydeAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel
HCID 8857
Ethyl Acetate
Lösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

263 mg (0.969 mmol) of mercuric chloride and 129 mg (1.29 mmol) of calcium carbonate were added to a suspension of 90 mg (0.323 mmol) of 2-(1-phenylcyclopentyl)methyl-1,3-dithiane [prepared as described in step (iv) above] in a mixture of 4 ml of acetonitrile and 0.6 ml of water, and the resulting mixture was stirred for 3 hours at 90° C. At the end of this time, the reaction mixture was cooled and then diluted with ethyl acetate. The insoluble materials were filtered off from the diluted mixture with the help of Celite (trade mark) filter aid. The filtrate was then washed with a 1M aqueous solution of sodium acetate, with a saturated aqueous solution of ammonium chloride and with a saturated aqueous solution of sodium chloride, in that order. The organic phase was dried over anhydrous sodium sulfate, and the solvent was removed by distillation under reduced pressure. The resulting residue was purified by column chromatography through 5 g of silica gel, using methylene chloride as the eluent, to give 58.4 mg (yield 96%) of the title compound as a foam-like material.

Aufarbeitung

  1. temperatureAt the end of this time, the reaction mixture was cooled
  2. filtrationThe insoluble materials were filtered off from the diluted mixture with the help of Celite (trade mark)
  3. filtrationfilter aid
  4. washThe filtrate was then washed with a 1M aqueous solution of sodium acetate, with a saturated aqueous solution of ammonium chloride and with a saturated aqueous solution of sodium chloride, in that order
  5. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  6. customthe solvent was removed by distillation under reduced pressure
  7. customThe resulting residue was purified by column chromatography through 5 g of silica gel

Quellen und Nachweise

ORD-Eintrag
ord-eaccc944365d408a8dcb9f0c30a59d64
Quelldatensatz
uspto-grants-1996_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05534529

Notizen zur Reaktion

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