Water → N-(1,2-diphenylethyl)-2-methoxyaniline

HRID 41329Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 41329
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=1/[N:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:17]([Mg]Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>C1COCC1>[C:7]1([CH:6]([NH:5][C:4]2[CH:13]=[CH:14][CH:15]=[CH:16][C:3]=2[O:2][CH3:1])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 178418336HCID 178418336, VerbindungHCID 178489586HCID 178489586, Verbindung

Produkt 1

HCID 58238643N-(1,2-diphenylethyl)-2-methoxyanilineAusbeute 96,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-80 °C

Versuchsvorschrift

To a solution of 4.22 g (20.0 mmol) of 9 in 50 mL of THF, 48.0 mL (26.0 mmol) of 0.55 M BnMgCl in THF was added with vigorous stirring at −80° C. This mixture was slowly warmed to room temperature, and then 2 mL of water was added. The resulting mixture was evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-diethyl ether=40:1, vol.) to give 5.83 g (96%) of B3.

Aufarbeitung

  1. temperatureThis mixture was slowly warmed to room temperature
  2. customThe resulting mixture was evaporated to dryness
  3. customThe product was isolated by flash chromatography on silica gel 60 (40-63 um, eluent: from hexanes to hexanes-diethyl ether=40:1, vol.)

Quellen und Nachweise

ORD-Eintrag
ord-e2cbda05e6034070a2856d40446509c2
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530593B2

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