Cyclohexene → HCID 59444173, Verbindung

HRID 2070110Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2070110
[CH3:1][C:2]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([N+:14]([O-])=O)[CH:8]=2)[O:6][CH2:5][CH2:4][O:3]1.C1CCCCC=1>[Pd].C(O)C>[NH2:14][C:9]1[CH:8]=[C:7]([C:2]2([CH3:1])[O:3][CH2:4][CH2:5][O:6]2)[CH:12]=[CH:11][C:10]=1[OH:13]

Komponenten

5

Edukt 2

HCID 8079CyclohexeneHCID 190269674-(2-Methyl-1,3-dioxolan-2-yl)-2-nitrophenol

Produkt 1

HCID 59444173HCID 59444173, VerbindungAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A stirred mixture of 4-(2-methyl-1,3-dioxolan-2-yl)-2-nitrophenol D61 (2.40 g, 10.66 mmol), cyclohexene (4.38 g, 53.3 mmol) and 10% palladium on carbon (0.227 g, 0.213 mmol) in ethanol (75 mL) was heated to reflux for 6 hr under argon. The mixture was cooled to rt and the catalyst was removed by filtration through celite. The filtrate was concentrated to dryness in vacuo and the reside dissolved in 10% MeOH in DCM (20 mL) and passed through a SCX-2 cartridge (25 g) which was then eluted with further 10% MeOH in DCM to wash through any unreacted starting material and then with 2M ammonia in MeOH. The basic eluate was concentrated under vacuum to give the title compound as a yellow-brown solid (1.58 g, 76%).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 6 hr under argon
  3. customthe catalyst was removed by filtration through celite
  4. concentrationThe filtrate was concentrated to dryness in vacuo
  5. dissolutionthe reside dissolved in 10% MeOH in DCM (20 mL)
  6. washwas then eluted with further 10% MeOH in DCM
  7. washto wash through
  8. concentrationThe basic eluate was concentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1ef8d13ffb3b4550a69a5ae95e93fdb7
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299257B2

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