Imidazole → (R)-1-iodo-2,6-dimethyl heptane

HRID 28445

Reaktionsgleichung

Reaktionsgleichung von HRID 28445
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:20]I.N1C=CN=C1.[CH3:27][C@H:28]([CH2:31][CH2:32][CH2:33][CH:34]([CH3:36])[CH3:35])[CH2:29]O>C(Cl)Cl>[I:20][CH2:29][C@H:28]([CH3:27])[CH2:31][CH2:32][CH2:33][CH:34]([CH3:36])[CH3:35]

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 10558744(2R)-2,6-dimethylheptan-1-ol

Produkt 1

HCID 86589986(R)-1-iodo-2,6-dimethyl heptane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a mixture of supported triphenyl phosphine (6.55 g, 19.67 mmol) in CH2Cl2 at 0° C. was added iodine (4.99 g, 19.67 mmol) and imidazole (1.33 g, 19.67 mmol). The mixture was warmed to ambient temperature, stirred for 1 h and cooled to 0° C. for the dropwise addition of (R)-2,6-dimethyl heptan-1-ol in CH2Cl2 (5 mL). The mixture was allowed to reach ambient temperature and stirred for 1 h, at which time it was filtered through a pad of celite and the solids were washed with CH2Cl2. The filtrated was concentrated, and the crude product was purified via silica gel chromatography to give (R)-1-iodo-2,6-dimethyl heptane (2.44 g).

Aufarbeitung

  1. customto reach ambient temperature
  2. stirringstirred for 1 h, at which time it
  3. filtrationwas filtered through a pad of celite
  4. washthe solids were washed with CH2Cl2
  5. concentrationThe filtrated was concentrated
  6. customthe crude product was purified via silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-79cb949d838e4477b5d7a1551591ef04
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419981B2

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