Reaktion #435442

ord-ff0fec4095954dc18dfb60f298b58d96

Reaktionsgleichung

C=CC[C@H](C)[C@@H](CC(=O)C(C)(C)C(OC(C)C)OC(C)C)OC(=O)OCC(Cl)(Cl)Cl
(5R,6S)-1,1-diisopropoxy-5-(2,2,2-trichloroethoxycarbonyloxy)-2,2,6-trimethyl-8-nonen-3-one
Cc1ccc(S(=O)(=O)O)cc1.O
p-toluenesulfonic acid monohydrate
O=C([O-])O.[Na+]
NaHCO3
→
C=CC[C@H](C)[C@@H](CC(=O)C(C)(C)C=O)OC(=O)OCC(Cl)(Cl)Cl
(5R,6S)-3-oxo-5-(2,2,2-trichloroethoxycarbonyloxy)-2,2,6-trimethyl-8-nonenal

Edukte

C=CC[C@H](C)[C@@H](CC(=O)C(C)(C)C(OC(C)C)OC(C)C)OC(=O)OCC(Cl)(Cl)Cl
(5R,6S)-1,1-diisopropoxy-5-(2,2,2-trichloroethoxycarbonyloxy)-2,2,6-trimethyl-8-nonen-3-one
Cc1ccc(S(=O)(=O)O)cc1.O
p-toluenesulfonic acid monohydrate
O=C([O-])O.[Na+]
NaHCO3

Reagenzien

Keine

Lösungsmittel

C1CCOC1.O
THF water

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturis heated
  2. 2
    Temperaturat reflux for 7 hours
  3. 3
    TemperaturThe mixture is cooled
  4. 4
    Extraktionextracted with ethyl acetate
  5. 5
    TrocknenThe extract is dried over Na2SO4
  6. 6
    Filtrationfiltered
  7. 7
    Sonstigeevaporated
  8. 8
    SonstigeThe product is purified by chromatography on SiO2

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07176235B2uspto-grants-2007_02