Imidazole → (S)-8-Iodo-2,6-dimethyl-2-octene

HRID 466646

Reaktionsgleichung

Reaktionsgleichung von HRID 466646
[CH3:1][C:2](=[CH:4][CH2:5][CH2:6][C@@H:7]([CH2:9][CH2:10]O)[CH3:8])[CH3:3].N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:36]I>C1COCC1.CCCCCC>[I:36][CH2:10][CH2:9][C@@H:7]([CH3:8])[CH2:6][CH2:5][CH:4]=[C:2]([CH3:3])[CH3:1]

Komponenten

7

Edukt 4

HCID 795ImidazoleHCID 807IodineHCID 7793Beta-citronellol, (S)-HCID 11776Triphenylphosphine

Produkt 1

HCID 11207832(S)-8-Iodo-2,6-dimethyl-2-octeneAusbeute 79,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

A solution of 3.12 g (20.0 mmol) of (S)-(-)-β-citronellol (purchased from Aldrich Chem. Co.) and 2.72 g (40.0 mmol) of imidazole in 50 mL of THF at 0° C. was treated with 5.0 g (19.5 mmol) of triphenylphosphine followed by 4.83 g (19.0 mmol) of I2 in 25 mL of THF dropwise over 20 minutes. The reaction mixture was stirred for 1.0 hour and was diluted with hexane. The organic mixture was washed with aqueous Na2SO3, brine, dried (Na2SO4) and evaporated to provide a crude white slurry. The slurry was purified by flash chromatography (300 g of silica gel) eluting with hexane to provide 4.00 g (79%) of title iodide as a colorless oil.

Aufarbeitung

  1. washThe organic mixture was washed with aqueous Na2SO3, brine
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customto provide a crude white slurry
  5. customThe slurry was purified by flash chromatography (300 g of silica gel)
  6. washeluting with hexane

Quellen und Nachweise

ORD-Eintrag
ord-0824be1d0c9b43e890ce4acc0d6c7a8c
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05157027

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