4-Oxo-1-iodo-trans-1-octene → 4-Hydroxy-4-vinyl-1-iodo-trans-1-octene

HRID 66405

Reaktionsgleichung

Reaktionsgleichung von HRID 66405
[CH:1]([Mg]Cl)=[CH2:2].[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]([CH:1]=[CH2:2])([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 178461836HCID 178461836, Verbindung

Produkt 1

HCID 128512814-Hydroxy-4-vinyl-1-iodo-trans-1-octene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 7.8 ml of vinyl magnesium chloride (2.3M in tetrahydrofuran), at -25° C is added a solution of 3.55 g of 4-oxo-1-iodo-trans-1-octene in 20 ml of tetrahydrofuran during 15 minutes. After the addition, the solution is stirred at -20° C to -15° C for 30 minutes. The reaction is quenched with a mixture of hexane and ice. The aqueous phase is separated and extracted with additional hexane. The combined hexane extracts are washed successively with water and brine. The solution is dried over magnesium sulfate and concentrated. The residue is subjected to dry column chromatography on silica gel with benzene as developing solvent to give a liquid, pmr spectrum (CDCl3): 5.2 (m, terminal CH2), 5.83 (q, CH=CH2), 6.13 (d, ICH=), and 6.52 (m, ICM=CH).

Aufarbeitung

  1. additionAfter the addition
  2. customThe reaction is quenched with a mixture of hexane and ice
  3. customThe aqueous phase is separated
  4. extractionextracted with additional hexane
  5. washThe combined hexane extracts are washed successively with water and brine
  6. dry with materialThe solution is dried over magnesium sulfate
  7. concentrationconcentrated
  8. dry with materialto dry column chromatography on silica gel with benzene
  9. customto give a liquid, pmr spectrum (CDCl3)

Quellen und Nachweise

ORD-Eintrag
ord-f9e726b8d9a8457ebc9d5e69bdd57fd9
Quelldatensatz
uspto-grants-1978_12
Patentnummer
US04131737

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