2-Bromo-cyclopent-2-enol → 2-Isobutyl-cyclopent-2-enol

HRID 1393266

Reaktionsgleichung

Reaktionsgleichung von HRID 1393266
Br[C:2]1[CH:3]([OH:7])[CH2:4][CH2:5][CH:6]=1.[CH2:8]([Mg]Br)[CH:9]([CH3:11])[CH3:10]>C1COCC1.[Ni](Cl)Cl.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:8]([C:2]1[CH:3]([OH:7])[CH2:4][CH2:5][CH:6]=1)[CH:9]([CH3:11])[CH3:10]

Komponenten

5

Edukt 2

HCID 111374622-Bromo-cyclopent-2-enol2×HCID 178418816HCID 178418816, Verbindung

Produkt 1

HCID 219862102-Isobutyl-cyclopent-2-enol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2724937Dichloro(1,1'-(1,3-propanediyl)bis(1,1-diphenylphosphine-kappaP))nickelKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The alcohol (Intermediate D3, 16 mmol) in THF (30 mL) at 0° C. was treated with isobutyl magnesium bromide (40 mmol). The catalyst, 1,3-bis(diphenylphosphino)propane nickel (II) chloride (0.75 mmol) (NiCl2dppp) was added in one portion and the mixture was heated to reflux for 3 h. (see: Organ et al. J. Org. Chem. 1997, 62, 1523, incorporated herein by reference). The reaction mixture was cooled to rt and quenched with sat. NH4Cl solution. The mixture was filtered and partitioned between brine and diethyl ether. The organic layer was removed and dried over Na2SO4, filtered and concentrated under vacuum. The oil was purified by chromatography on SiO2 with 20% EtOAc:Hx to yield 2-isobutyl-cyclopent-2-enol (Intermediate D4). Use of 2-isobutyl-cyclopent-2-enol (Intermediate D4) in Method A produced 4-(2-isobutyl-cyclopent-2-enylmethyl)-1,3-dihydro-imidazole-2-thione (Compound 20).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 h. (
  3. customquenched with sat. NH4Cl solution
  4. filtrationThe mixture was filtered
  5. custompartitioned between brine and diethyl ether
  6. customThe organic layer was removed
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customThe oil was purified by chromatography on SiO2 with 20% EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-01f9c3eee9894caf88f9802cf277b36c
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07345077B2

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