Chloroform → 4-(4-Methoxyphenyl)morpholine

HRID 1014785

Reaktionsgleichung

Reaktionsgleichung von HRID 1014785
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.CC([O-])(C)C.[Na+].C(Cl)(Cl)Cl>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2[C-](N(C)C)C=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2]>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:3][CH:4]=1

Komponenten

8

Edukt 4

HCID 6212ChloroformHCID 77304-BromoanisoleHCID 8083MorpholineHCID 23676156Sodium t-butoxide

Produkt 1

HCID 3898744-(4-Methoxyphenyl)morpholineAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1317290462-Diphenylphosphino-dimethylaminoferroceneKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

According to General Procedure B, a mixture of 4-bromoanisole (63 μL, 0.50 mmol), morpholine (52 μL, 0.60 mmol), NaOt-Bu (67 mg, 0.70 mmol), Pd2(dba)3.CHCl3 (10 mg, 0.01 mmol), and 12f (8 mg, 0.02 mmol) in PhMe (2.5 mL) was heated, cooled and filtered. Evaporation of the solvent under reduced pressure and column chromatography of the pre-adsorbed crude material (2:50:48 Et3N/Et2O/hexane, silica gel) gave 52e (64 mg, 67%) as an off-white solid. 1H NMR (300 MHz, CDCl3) δ 6.92-6.84 (m, 4H), 3.86 (t, 4H, J=4.8 Hz), 3.77 (s, 3H), 3.06 (t, 4H, J=4.8 Hz); 13C NMR (75.5 MHz, CDCl3) δ 153.9, 145.5, 117.7, 114.4, 66.9, 55.5, 50.7.

Aufarbeitung

  1. temperaturecooled
  2. filtrationfiltered
  3. customEvaporation of the solvent under reduced pressure and column chromatography of the pre-adsorbed crude material (2:50:48 Et3N/Et2O/hexane, silica gel)

Quellen und Nachweise

ORD-Eintrag
ord-7ff1dd8692fc4e1084019b4bdd77e28e
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07982064B2

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