Tetrahydrofuran → Methyl 2-(4-aminomethylphenyl)-2-methylpropionate

HRID 1282117Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1282117
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([CH3:17])([CH3:16])[C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1>O>[NH2:1][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([CH3:17])([CH3:16])[C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 18423002Methyl 2-(4-azidomethylphenyl)-2-methylpropionate

Produkt 1

HCID 18423094Methyl 2-(4-aminomethylphenyl)-2-methylpropionateAusbeute 68,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of methyl 2-(4-azidomethylphenyl)-2-methylpropionate (48.1 g)and triphenylphosphine (59.5 g) in a mixed solvent of tetrahydrofuran (480 ml) and water (24 ml) was refluxed for 30 min. The solvent was evaporated, and the obtained residue was purified by silica gel column chromatography (developing solvent; chloroform:methanol=10:1, chloroform:methanol:aqueous ammonia=10:1:0.3) to give the title compound (29.4 g) as a pale-yellow oil.

Aufarbeitung

  1. customThe solvent was evaporated
  2. customthe obtained residue was purified by silica gel column chromatography (developing solvent; chloroform:methanol=10:1, chloroform:methanol:aqueous ammonia=10:1:0.3)

Quellen und Nachweise

ORD-Eintrag
ord-e1e5902d689740869b94c8493756d9eb
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06455528B1

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