Isopropanol → 3-Methoxy-5-(propan-2-yloxy)aniline

HRID 1616945Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1616945
[NH2:1][C:2]1[CH:3]=[C:4](O)[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.[CH:11]([OH:14])([CH3:13])[CH3:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH:11]([O:14][C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([O:8][CH3:9])[CH:5]=1)[NH2:1])([CH3:13])[CH3:12]

Komponenten

6

Edukt 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 119535163-Amino-5-methoxyphenol

Produkt 1

HCID 115719053-Methoxy-5-(propan-2-yloxy)anilineAusbeute 58,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-amino-5-methoxyphenol (5.44 g, 39.1 mmol), isopropyl alcohol (3.6 ml, 47 mmol) and triphenylphosphine (12.0 g, 47 mmol) in THF, was added diethyl azodicarboxylate (7.4 ml, 47 mmol). The reaction mixture was stirred for 16 h and the solvent was removed. The residue was purified by flash chromatography on silica gel eluting with 20% EtOAc/hexanes to afford the title compound (4.13 g). MS m/z: 182 [M+H]+

Aufarbeitung

  1. customthe solvent was removed
  2. customThe residue was purified by flash chromatography on silica gel eluting with 20% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-689972f5ed864150a37c67ba9247ea6a
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765779B2

Notizen zur Reaktion

Wird geladen…