4-Oxo-1-iodo-trans-1-octene → 4-Hydroxy-4-(1-propynyl)-1-iodo-trans-1-octene

HRID 1413574Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1413574
[C:1]([Li])#[C:2][CH3:3].[O:5]=[C:6]([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:7]/[CH:8]=[CH:9]/[I:10]>O1CCCC1>[OH:5][C:6]([C:1]#[C:2][CH3:3])([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:7]/[CH:8]=[CH:9]/[I:10]

Komponenten

4

Edukt 2

HCID 128512804-Oxo-1-iodo-trans-1-octeneHCID 178506788HCID 178506788, Verbindung

Produkt 1

HCID 205650814-Hydroxy-4-(1-propynyl)-1-iodo-trans-1-octene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of propynyllithium at -25° is added a solution of 4-oxo-1-iodo-trans-1-octene in tetrahydrofuran. After the addition, the solution is stirred at -20° to -15° C. for 30 minutes. Tbe reaction is quenched with a mixture of hexane and ice. The aqueous phase is separated and extracted with additional hexane. The combined hexane extracts is washed successively with water and brine. The solution is dried over magnesium sulfate and concentrated. The residue is chromatographed on a silica gel column and is eluted with tolulene to provide the product as an oil.

Aufarbeitung

  1. additionAfter the addition
  2. customTbe reaction
  3. customis quenched with a mixture of hexane and ice
  4. customThe aqueous phase is separated
  5. extractionextracted with additional hexane
  6. washThe combined hexane extracts is washed successively with water and brine
  7. dry with materialThe solution is dried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue is chromatographed on a silica gel column
  10. washis eluted with tolulene

Quellen und Nachweise

ORD-Eintrag
ord-9dd63f5884b44e9280b8ede1ad804e75
Quelldatensatz
uspto-grants-1981_02
Patentnummer
US04250325

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