Pyridine → (5R,6S)-1,1-diisopropoxy-5-(2,2,2-trichloroethoxycarbonyloxy)-2,2,6-trimethyl-8-nonen-3-one

HRID 2181765Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2181765
Cl[C:2]([O:4][CH2:5][C:6]([Cl:9])([Cl:8])[Cl:7])=[O:3].N1C=CC=CC=1.[CH:16]([O:19][CH:20]([O:34][CH:35]([CH3:37])[CH3:36])[C:21]([CH3:33])([CH3:32])[C:22](=[O:31])[CH2:23][C@@H:24]([OH:30])[C@@H:25]([CH3:29])[CH2:26][CH:27]=[CH2:28])([CH3:18])[CH3:17].[Na+].[Cl-]>C(Cl)Cl>[CH:35]([O:34][CH:20]([O:19][CH:16]([CH3:18])[CH3:17])[C:21]([CH3:32])([CH3:33])[C:22](=[O:31])[CH2:23][C@@H:24]([O:30][C:2]([O:4][CH2:5][C:6]([Cl:9])([Cl:8])[Cl:7])=[O:3])[C@@H:25]([CH3:29])[CH2:26][CH:27]=[CH2:28])([CH3:37])[CH3:36]

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 5234Sodium ChlorideHCID 870632,2,2-Trichloroethyl chloroformateHCID 86586620(5R,6S)-1,1-diisopropoxy-5-hydroxy-2,2,6-trimethyl-8-nonen-3-one

Produkt 1

HCID 86586619(5R,6S)-1,1-diisopropoxy-5-(2,2,2-trichloroethoxycarbonyloxy)-2,2,6-trimethyl-8-nonen-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Trichloroethyl chloroformate (2.5 mL) and pyridine (2.95 mL) are added to a solution of (5R,6S)-1,1-diisopropoxy-5-hydroxy-2,2,6-trimethyl-8-nonen-3-one (2.9 g) in 40 mL of CH2Cl2 at 0° C., and the mixture is stirred for 5 hours before pouring into sat. aq. NaCl and extracting with CH2Cl2. The extract is dried over Na2SO4, filtered, and evaporated. The product is purified by chromatography on SiO2.

Aufarbeitung

  1. extractionextracting with CH2Cl2
  2. dry with materialThe extract is dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe product is purified by chromatography on SiO2

Quellen und Nachweise

ORD-Eintrag
ord-35ba18c8ce0241e49079962ee61ed390
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06893859B2

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