Iodine → 1-Iodo-4-trimethylsiloxy-trans-1-octene

HRID 66402

Reaktionsgleichung

Reaktionsgleichung von HRID 66402
CC(C)C(BC(C(C)C)C)C.[CH3:12][Si:13]([CH3:24])([CH3:23])[O:14][CH:15]([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:16][C:17]#[CH:18].C[N+]([O-])(C)C.[OH-].[Na+].[I:32]I>O1CCCC1>[I:32]/[CH:18]=[CH:17]/[CH2:16][CH:15]([O:14][Si:13]([CH3:23])([CH3:24])[CH3:12])[CH2:19][CH2:20][CH2:21][CH3:22]

Komponenten

7

Edukt 5

HCID 807IodineHCID 1145Trimethylamine oxideHCID 14798Sodium HydroxideHCID 192733Bis(1,2-dimethylpropyl)boraneHCID 12786181Trimethyl[(oct-1-yn-4-yl)oxy]silane

Produkt 1

HCID 128512771-Iodo-4-trimethylsiloxy-trans-1-octene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To a stirred solution of 0.020 moles of freshly prepared bis-(3-methyl-2-butyl)borane in 300 ml of tetrahydrofuran at 0°-5° C is added dropwise a solution of 19.8 g of 4-trimethylsiloxy-1-octyne in 30 ml of tetrahydrofuran. The resulting mixture is stirred at ambient temperature for several hours, cooled in an ice bath, and treated with 53 g of trimethylamine oxide. The mixture is stirred several hours at 25°-40° C and then poured into 2 liters of 15% sodium hydroxide. The resulting mixture is treated immediately with a solution of 140 g of iodine in 300 ml of tetrahydrofuran. After 0.5 hour the organic phase is separated and the aqueous phase is extracted with ether. The combined organic layers are washed with water, sodium thiosulfate solution, and brine; dried over magnesium sulfate; and concentrated to give an oil, pmr spectrum (CDCl 3): 6.2 (d, ICH=) and 6.7 (quintuplet, =C-).

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. stirringThe mixture is stirred several hours at 25°-40° C
  3. customAfter 0.5 hour the organic phase is separated
  4. extractionthe aqueous phase is extracted with ether
  5. washThe combined organic layers are washed with water, sodium thiosulfate solution, and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationand concentrated
  8. customto give an oil, pmr spectrum (CDCl 3)

Quellen und Nachweise

ORD-Eintrag
ord-ee8814a93a8044e3904426eff2a6053d
Quelldatensatz
uspto-grants-1978_12
Patentnummer
US04131737

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