Diiodomethane → 1-[2-(Cyclopropylmethoxy)ethyl]-4-(phenylmethoxy)benzene

HRID 1745867Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1745867
[CH2:1]([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)[CH:2]=[CH2:3].I[CH2:22]I>CCOCC>[CH2:14]([O:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][O:4][CH2:1][CH:2]2[CH2:22][CH2:3]2)=[CH:8][CH:9]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

4

Edukt 2

HCID 6346DiiodomethaneHCID 22227278HCID 22227278, Verbindung

Produkt 1

HCID 115146971-[2-(Cyclopropylmethoxy)ethyl]-4-(phenylmethoxy)benzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a suspension of Zn/Cu couple (3.24 g) and dry ether (20 ml) was added to the compound of formula (7), (2 g, 0.0075 mol) in ether (10 ml) followed by the addition of diiodomethane (4.2 ml, 0.052 mol). The reaction mixture was refluxed under nitrogen atmosphere for 72 h (monitored by TLC) and filtered. The filtrate was washed with water, dried, concentrated and the residue purified by column chromatography on silica gel, eluting with light petroleum ether:ethyl acetate(2:50) to afford pure product of formula (8), as an oil 1.8 g (85%).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed under nitrogen atmosphere for 72 h (monitored by TLC)
  2. filtrationfiltered
  3. washThe filtrate was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customthe residue purified by column chromatography on silica gel
  7. washeluting with light petroleum ether:ethyl acetate(2:50)

Quellen und Nachweise

ORD-Eintrag
ord-44b25bb211304a6981e5249bc99ac7bc
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07019172B2

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