Diiodomethane → 4-(1-Methylcyclopropyl)cyclohexanone

HRID 1419808Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1419808
[C:1]([CH:4]1[CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]1)([CH3:3])=[CH2:2].[CH2:11]([Zn]CC)C.ICI.[NH4+].[Cl-]>CCCCCC>[CH3:2][C:1]1([CH:4]2[CH2:9][CH2:8][C:7](=[O:10])[CH2:6][CH2:5]2)[CH2:11][CH2:3]1

Komponenten

6

Edukt 4

HCID 6346DiiodomethaneHCID 25517Ammonium ChlorideHCID 5492914-(1-Methylethenyl)cyclohexanoneHCID 178418750HCID 178418750, Verbindung

Produkt 1

HCID 541016014-(1-Methylcyclopropyl)cyclohexanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-60 °C

Versuchsvorschrift

5.0 g (0.036 mol) of 4-isopropenylcyclohexanone (precursor to Example 4) were placed under inert gas in 150 ml of hexane, and 16.5 g (0.134 mol) of diethylzinc (1M in hexane) followed by 58.0 g (0.22 mol) of diiodomethane were added dropwise at -20° C. The mixture was stirred at -60° C. for 2 hours and then at 0° C. for 6 hours. The reaction solution was kept in a refrigerator overnight and was worked up by pouring it into cold NH4Cl solution and carrying out extraction with ether. The organic phase was washed with sodium thiosulfate solution and water, dried and concentrated. 5.3 g (96% of theory) of a colorless oil were obtained which was reacted without further purification.

Aufarbeitung

  1. additionwere added dropwise at -20° C
  2. waitat 0° C. for 6 hours
  3. customwas kept in a refrigerator overnight
  4. extractionextraction with ether
  5. washThe organic phase was washed with sodium thiosulfate solution and water
  6. customdried
  7. concentrationconcentrated
  8. custom5.3 g (96% of theory) of a colorless oil were obtained which
  9. customwas reacted without further purification

Quellen und Nachweise

ORD-Eintrag
ord-1527b35168534654a5c8f8b41ab5f3a1
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05889012

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