Potassium Carbonate → HCID 86760619, Verbindung

HRID 2057331Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2057331
[CH2:1]([O:8][C:9](=[O:20])[N:10]([C@H:12]1[CH2:17][CH2:16][C@H:15]([CH:18]=O)[CH2:14][CH2:13]1)[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br-].[Br:22][CH2:23][CH2:24][CH2:25][CH2:26][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CC(O)(CC)C>[CH2:1]([O:8][C:9](=[O:20])[N:10]([CH:12]1[CH2:17][CH2:16][CH:15]([CH:18]=[CH:26][CH2:25][CH2:24][CH2:23][Br:22])[CH2:14][CH2:13]1)[CH3:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 2733851(4-Bromobutyl)triphenylphosphanium bromideHCID 178485996HCID 178485996, Verbindung

Produkt 1

HCID 86760619HCID 86760619, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 64052-Methyl-2-butanolLösungsmittel

Versuchsvorschrift

A solution of 126.5 g (459.4 mmol) of trans-(4-Formyl-cyclohexyl)-methyl-carbamic acid benzyl ester in 1.27 l 2-methyl-2-butanol was treated with 263.6 g (551.3 mmol) (4-bromobutyl)triphenylphosphonium bromide and 254 g (1838 mmol) of K2CO3 and was heated at reflux for 3.5 h. The reaction was cooled (RT), filtered and evaporated. The residue was suspended in hexane (1.8 l, first at RT then at 0° C.) and filtered. Purification by column chromatography on silica gel (hexane/EtOAc 4:1) gave 149.9 g (83%) of trans-(1 E/Z)-[4-(5-Bromo-pent-1-enyl)-cyclohexyl]-methyl-carbamic acid benzyl ester, MS: 293 (M, 1Br).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 3.5 h
  3. filtrationfiltered
  4. customevaporated
  5. filtrationfirst at RT then at 0° C.) and filtered
  6. customPurification by column chromatography on silica gel (hexane/EtOAc 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-4005ec2e19c74c5c82a97a7853be0a42
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07335687B2

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