Bicyclo[3.1.0]hexan-2-ol → HCID 131710021, Verbindung

HRID 436345Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 436345
[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)CCCCC.C([Li])CCC.[CH:32]12[CH2:37][CH:36]1[CH2:35][CH:34]([OH:38])[CH2:33]2.[CH:39]12C[CH:43]1[CH2:42][CH2:41][CH:40]2[OH:45]>CCCCCC.C1C=CC=CC=1>[O:45]1[CH2:39][CH2:43][CH2:42][CH2:41][CH:40]1[O:38][CH:34]1[CH2:35][CH:36]2[CH:32]([CH2:37]2)[CH2:33]1

Komponenten

7

Edukt 4

HCID 276343Bicyclo[3.1.0]hexan-2-olHCID 2724569Phosphonium, hexyltriphenyl-, bromide (1:1)HCID 12724622Bicyclo[3.1.0]hexan-3-olHCID 178418339Butyllithium

Produkt 1

HCID 131710021HCID 131710021, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittel2×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A mixture of hexyltriphenylphosphonium bromide (102 g.) and benzene (1200 ml.) is stirred under nitrogen during addition of a solution of butyl lithium in hexane (146 ml. of a 15% solution - w/v). The resulting mixture is stirred 30 minutes. Then a solution of the mixture (27 g.) of products obtained according to Preparation 4 in 300 ml. of benzene is added dropwise with stirring during 30 minutes. The mixture is heated and stirred at 70° C. for 2.5 hours, and then is cooled to 25° C. The resulting precipitate is collected by filtration and washed with benzene. The filtrate and benzene wash are combined, washed with water, dried, and evaporated to give 58 g. of a mixture of the tetrahydropyranyl ethers of endo-6-(cis- and trans-1-heptenyl)bicyclo[3.1.0]hexan-3-ol and endo-6-(cis- and trans-1-heptenyl)bicyclo[3.1.0]hexan-2-ol.

Aufarbeitung

  1. customThen a solution of the mixture (27 g.) of products obtained
  2. customaccording to Preparation 4 in 300 ml
  3. stirringwith stirring during 30 minutes
  4. temperatureThe mixture is heated
  5. stirringstirred at 70° C. for 2.5 hours
  6. filtrationThe resulting precipitate is collected by filtration
  7. washwashed with benzene
  8. washThe filtrate and benzene wash
  9. washwashed with water
  10. customdried
  11. customevaporated
  12. customto give 58 g

Quellen und Nachweise

ORD-Eintrag
ord-b154fc446dcb4e3ea497f6803f4b0908
Quelldatensatz
uspto-grants-1977_02
Patentnummer
US04008263

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