4-[(2e)-3-(4-Bromophenyl)prop-2-enoyl]morpholine → 3-(4-Bromophenyl)-1-morpholinopropan-1-one

HRID 270016

Reaktionsgleichung

Reaktionsgleichung von HRID 270016
[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[O:11])=[CH:4][CH:3]=1>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh].C(OCC)(=O)C.C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)=[O:11])=[CH:4][CH:3]=1

Komponenten

4

Edukt 1

HCID 60401964-[(2e)-3-(4-Bromophenyl)prop-2-enoyl]morpholine

Produkt 1

HCID 221798563-(4-Bromophenyl)-1-morpholinopropan-1-oneAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)KatalysatorHCID 21584252Ethanol ethylacetateLösungsmittel

Versuchsvorschrift

A solution of Example 4A (4.405 mmol) in 1:1 ethyl acetate/ethanol (50 mL) was treated with Wilkinson's catalyst (815 mg, 0.880 mmol), degassed three times by freeze-thaw cycle, heated to reflux under nitrogen atmosphere for 2 days, and cooled to room temperature. The solution was adsorbed onto silica gel and purified by flash column chromatography with 50% ethyl acetate in hexane to provide the desired product (1.024 g, 78%). 1H NMR (300 MHz, CD3OD) δ 7.40 (2H, d), 7.10 (2H, d), 3.62 (4H, m), 3.57 (2H, t), 3.38 (2H, t), 2.94 (2H, t), 2.58 (2H, t).

Aufarbeitung

  1. customdegassed three times by freeze-thaw cycle
  2. temperatureheated
  3. temperatureto reflux under nitrogen atmosphere for 2 days
  4. custompurified by flash column chromatography with 50% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-4ef4f2b7c7ae489589a4d69e00d1c411
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449485B2

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