Sodium Bicarbonate → (5R,6S)-3-oxo-5-(2,2,2-trichloroethoxycarbonyl-oxy)-2,2,6-trimethyl-8-nonenal

HRID 2296866Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2296866
C([O:4][CH:5](OC(C)C)[C:6]([CH3:26])([CH3:25])[C:7](=[O:24])[CH2:8][C@@H:9]([O:15][C:16]([O:18][CH2:19][C:20]([Cl:23])([Cl:22])[Cl:21])=[O:17])[C@@H:10]([CH3:14])[CH2:11][CH:12]=[CH2:13])(C)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C1COCC1.O>[O:24]=[C:7]([CH2:8][C@@H:9]([O:15][C:16]([O:18][CH2:19][C:20]([Cl:21])([Cl:22])[Cl:23])=[O:17])[C@@H:10]([CH3:14])[CH2:11][CH:12]=[CH2:13])[C:6]([CH3:26])([CH3:25])[CH:5]=[O:4]

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 86586619(5R,6S)-1,1-diisopropoxy-5-(2,2,2-trichloroethoxycarbonyloxy)-2,2,6-trimethyl-8-nonen-3-one

Produkt 1

HCID 59922918(5R,6S)-3-oxo-5-(2,2,2-trichloroethoxycarbonyl-oxy)-2,2,6-trimethyl-8-nonenal

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

A mixture of (5R,6S)-1,1-diisopropoxy-5-(2,2,2-trichloroethoxycarbonyloxy)-2,2,6-trimethyl-8-nonen-3-one (4.3 g) and p-toluenesulfonic acid monohydrate (0.45 g) in 100 mL of 3:1 THF/water is heated at reflux for 7 hours. The mixture is cooled and poured into sat. aq. NaHCO3, then extracted with ethyl acetate. The extract is dried over Na2SO4, filtered, and evaporated. The product is purified by chromatography on SiO2.

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux for 7 hours
  3. temperatureThe mixture is cooled
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract is dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe product is purified by chromatography on SiO2

Quellen und Nachweise

ORD-Eintrag
ord-988365bd04604c24894956a009cba339
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06489314B1

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