Methanol → Methyl 2-(4-(methylamino)phenyl)acetate

HRID 1039863Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1039863
[CH:1]([NH:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:6][CH:5]=1)=O.CSC.B.CO>C1COCC1>[CH3:1][NH:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 12423031(Dimethyl sulfide)trihydroboronHCID 86634878HCID 86634878, Verbindung

Produkt 1

HCID 15892780Methyl 2-(4-(methylamino)phenyl)acetateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of methyl (4-formylaminophenyl)acetate (4.31 g) in THF (20.0 mL) at 0° C. was slowly added borane dimethylsulfide (8.61 mL, 90.8 mmol). The reaction mixture was stirred at room temperature overnight and then cooled to 0° C. MeOH (15 mL) was added cautiously and the resulting mixture was stirred for 3 h. The mixture was then concentrated under reduced pressure to give the title compound (4.0 g, 73% yield, 2 steps) as a clear oil.

Aufarbeitung

  1. customat 0° C.
  2. temperaturecooled to 0° C
  3. stirringthe resulting mixture was stirred for 3 h
  4. concentrationThe mixture was then concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-38a6d24461bf4df38d75a4ab422ebbc6
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08551978B2

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