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1,2-Dichloroethane → HCID 58762226, Verbindung

HRID 858570
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 858570
Cl.[CH3:2][NH:3][O:4][CH3:5].C(Cl)CCl.C(N(CC)CC)C.[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27]([OH:29])=O)=[CH:21][CH:20]=1>>[CH3:5][O:4][N:3]([CH3:2])[C:27](=[O:29])[CH2:26][CH2:25][C:22]1[CH:21]=[CH:20][C:19]([O:18][CH3:17])=[CH:24][CH:23]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 957503-(p-Methoxyphenyl)propionic acid

Produkt 1

HCID 58762226HCID 58762226, VerbindungAusbeute 85,5 %

Versuchsvorschrift

N,O-dimethylhydroxylamine hydrochloride (5.41 g, 55.5 mmol), EDC (12.77 g, 66.6 mmol), followed by triethylamine (17 mL, 122 mmol) were added to a cooled 0° C. solution of 3-(4-methoxyphenyl)propionic acid (10 g, 55.5 mmol). The reaction mixture was stirred for 15 h under N2 and then concentrated. The residue was partitioned between 1 N HCl and EtOAc. The organic layers were washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated to an oil. The oil was purified by silica gel chromatography (40% EtOAc in hexanes) to give a clear oil (10.6 g, 85%).

Aufarbeitung

  1. concentrationconcentrated
  2. customThe residue was partitioned between 1 N HCl and EtOAc
  3. washThe organic layers were washed with saturated NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to an oil
  6. customThe oil was purified by silica gel chromatography (40% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-ae51d258e3424a28a3f351c218b701b6
Quelldatensatz
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07148226B2

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