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

HRID 1357420Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1357420
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-959a4d20f6b547a1bbb74e8ea5b0e168
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06589968B2

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